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Chemical Structure| 36476-87-6
Chemical Structure| 36476-87-6
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Product Details of [ 36476-87-6 ]

CAS No. :36476-87-6 MDL No. :MFCD01566539
Formula : C17H17NO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BRSCYENHLCPOAU-UHFFFAOYSA-N
M.W : 267.32 Pubchem ID :2735440
Synonyms :

Safety of [ 36476-87-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 36476-87-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 36476-87-6 ]

[ 36476-87-6 ] Synthesis Path-Downstream   1~12

  • 3
  • [ 36476-87-6 ]
  • [ 74-88-4 ]
  • [ 53871-06-0 ]
YieldReaction ConditionsOperation in experiment
80.8% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 20.5h; Potassium carbonate (6.53 g) and iodomethane (0.976 ml) were added to a solution of <strong>[36476-87-6]1-benzhydrylazetidine-3-carboxylic acid</strong> (4.20 g) in N,N-dimethylformamide (45 ml), followed by stirring at room temperature for 20.5 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=5:1, then 3:1). The fractions containing the target compound were concentrated to give the title compound (3.57 g, 80.8%) as yellow crystals.1H-NMR Spectrum (CDCl3) δ (ppm): 3.26 (2H, m), 3.31 (1H, m), 3.44 (2H, m), 3.69 (3H, s), 4.38 (1H, s), 7.16-7.20 (2H, m), 7.25-7.28 (4H, m), 7.39-7.41 (4H, m).ESI-MS (m/z): 282[M+H]+.
80.8% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 20.5h; (Production Example 84) Methyl 1-benzhydrylazetidine-3-carboxylate A solution of <strong>[36476-87-6]1-benzhydrylazetidine-3-carboxylic acid</strong> (4.20 g) in N,N-dimethylformamide (45 ml) were added potassium carbonate (6.53 g) and iodomethane (0.976 ml), followed by stirring at room temperature for 20.5 hr. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate = 5:1, then 3:1). Fractions containing the target compound were concentrated to provide the titled compound as yellow crystals (3.57 g, 80.8 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 3.26 (2H, m), 3.31 (1H, m), 3.44 (2H, m), 3.69 (3H, s), 4.38 (1H, s), 7.16-7.20 (2H, m), 7.25-7.28 (4H, m), 7.39-7.41 (4H, m). ESI-MS (m/z): 282 [M+H]+.
  • 4
  • [ 36476-87-6 ]
  • azetidine hydrochloride [ No CAS ]
  • [ 928038-41-9 ]
YieldReaction ConditionsOperation in experiment
65% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; 1-Benzhydrylazetidine-3-carboxylic acid (1.52 g) was dissolved in N,N-dimethylformamide (30 ml) at room temperature under a nitrogen atmosphere. Triethylamine (3.17 ml), BOP reagent (benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate; 5.03 g) and azetidine hydrochloride (1.06 g) were added in this order, followed by stirring for 24 hours. A 1N aqueous solution of sodium hydroxide (50 ml) was added to the reaction mixture, followed by stirring. Then the reaction mixture was extracted after addition of ethyl acetate (100 ml). The separated organic layer was washed with a 1N aqueous solution of sodium hydroxide, water and brine, and dried over anhydrous sodium sulfate. To the residue (1.83 g) obtained by distilling off the solvent were added ethyl acetate (2 ml) and tert-butyl methyl ether (10 ml) to precipitate crystals. The crystals were collected by filtration, and dried under aeration to give the title compound (1.14 g, 65%) as pale yellow crystals.1H-NMR Spectrum (CDCl3) δ (ppm): 2.15-2.30 (2H, m), 3.20-3.50 (5H, m), 3.90-4.10 (4H, m), 4.45 (1H, s), 7.15-7.45 (10H, m).ESI-MS (m/z): 307[M+H]+.
65% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; (Production Example 99) 3-(Azetidin-1-ylcarbonyl)-1-benzhydrylazetidine 1-Benzhydrylazetidine-3-carboxylic acid (1.52 g) was dissolved in N,N-dimethylformamide (30 ml) at room temperature under a nitrogen atmosphere. Triethylamine (3.17 ml), BOP reagent (5.03 g), and azetidine hydrochloride (1.06 g) were added in this order, followed by stirring for 24 hr. To the reaction mixture was added a 1N aqueous solution of sodium hydroxide (50 ml), followed by stirring. The liquid-liquid separation was carried out after addition of ethyl acetate (100 ml). The separated organic layer was washed with a 1N aqueous solution of sodium hydroxide, water and brine in this order, and dried over anhydrous sodium sulfate. To the residue (1.83 g) obtained by removing the solvent were added ethyl acetate (2 ml) and tert-butyl methyl ether (10 ml) to precipitate crystals. The crystals were collected by filtration and dried under aeration to provide the titled compound as pale yellow crystals (1.14 g, 65 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 2.15-2.30 (2H, m), 3.20-3.50 (5H, m), 3.90-4.10 (4H, m), 4.45 (1H, s), 7.15-7.45 (10H, m). ESI-MS (m/z): 307 [M+H]+.
  • 5
  • [ 36476-87-6 ]
  • [ 1068-57-1 ]
  • [ 1009368-02-8 ]
YieldReaction ConditionsOperation in experiment
95% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; Compound 34A. N'-acetyl-l-benzhydrylazetidine-S-carbohydrazidev y Ph HN-NH v Phλ[00217] To a solution of l-benzhydrylazetidine-3-carboxylic acid (2.097 g, 7.845 mmol) and acetohydrazine (0.967 g, 11.767 mmol) in DMF (40 mL) was added HOBt (1.59 g, 11.767 mmol) and EDAC (2.255 g, 11.767 mmol), followed by /-Pr2NEt (2.1 mL, 11.767 mmol). The mixture was stirred at room temperature overnight. Solvent was removed and the residue was purified via Prep HPLC to provide compound 34A as white solid (2.4 g, 95% yield). LC/MS (m/z) = 324 (M+H)+. 1H NMR (400 MHz, CDCl3) δ ppm 7.48 (d, J=7.1 Hz, 4 H), 7.28 - 7.42 (m, 6 H), 5.40 (s, 1 H), 4.30 (br. s., 2 H), 3.84 - 4.10 (m, 3 H), 1.84 - 2.07 (m, rotomer, 3 H).
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h; To 1 -benzhydrylazetidine-3-carboxyl ic acid (prepared according to patent US2008/2 14815Al, page 73 exampe 83) in DCM (10 mL) was added acetohydrazide (commerciallyavailable) and triethylamine (2.321 mL, 16.65 mmol) followed by T3P 50% in DMF (2.92 mL, 5.00 mmol) dropwise and the mixture was stirred at room temperature for 2 h. T3P (50% in DMF) (2.92 mL, 5.00 mmol), was added and the mixture was stirred for a further 1 h. The resulting mixture was partitioned between EtOAc and water and the aqueous layer wasremoved. The organic layer was washed with saturated sodium bicarbonate solution, water, brine and dried using a phase separating column. The solvent was removed under reduced pressure. Purification of the crude product by chromatography on silica using a gradient from 0 - 100% EtOAc in iso-hexane followed by methanol in EtOAc (10%) afforded the title compound as a yellow oil that solidified. The crude product was used in the next step withoutfurther purification.
  • 6
  • [ 6638-79-5 ]
  • [ 36476-87-6 ]
  • [ 359402-66-7 ]
YieldReaction ConditionsOperation in experiment
55% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 1h; 1- [3- (Dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (8.0 g, 42 mmol) was added to a suspension of1-benzhydryl-azetidine-3-carboxylic acid (7.42 g, 27.8 mmol), NO-dimethyl-hydroxyl-amine hydrochloride (4.24g, 43.5 mmol), and triethylamine (11.6mil, 83.3 mmol) in dichloromethane (150 mL). The suspension was then stirred at room temperature for 60 minutes. The suspension was diluted with dichloromethane (300 mL), and the resulting solution was washed with water (3 x 100 mL). The organic layer was then dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The resulting solid was purified via medium pressure liquid chromatography eluting with dichloromethane: methanol (40: 1) to deliver 4.76 g (55 % yield) of the title compound as a white solid (mp103-106 C) ; MS (APCI+):m/z 311(M+H) +.
55% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 1h; 1- [3- (Dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (8. 0 g, 42 mmol) was added to a suspension of1-benzhydryl-azetidine-3-carboxylic acid (7.42 g, 27.8 mmol), NO-dimethyl-hydroxyl-amine hydrochloride (4.24g, 43.5 mmol), and triethylamine (11.6 mL, 83.3 mmol) in dichloromethane (150 mL). The suspension was then stirred at room temperature for 60 minutes. The suspension was diluted with dichloromethane (300 mL), and the resulting solution was washed with water (3 x 100 mL). The organic layer was then dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The resulting solid was purified via medium pressure liquid chromatography eluting with dichloromethane: methanol (40: 1) to deliver 4.76 g (55 % yield) of the title compound as a white solid (mp103-106 C) ; MS (APCI+): m/z 311 (M+H)+.
  • 7
  • [ 36476-87-6 ]
  • [ 72351-36-1 ]
YieldReaction ConditionsOperation in experiment
54% 1-Benzhydryl-3-azetidinecarboxylic acid (3.12 g) was suspended in tetrahydrofuran (60 ml), and cooled in an ice-methanol bath under a nitrogen atmosphere. Triethylamine (1.96 ml) was added dropwise, and a solution of ethyl chlorocarbonate (1.34 ml) in tetrahydrofuran (5 ml) was added dropwise over 20 minutes. After the addition, the reaction mixture was stirred at the same temperature for 30 minutes. The reaction mixture was filtered, and the residue was washed with tetrahydrofuran (30 ml). The filtrate was added dropwise to a solution of an aqueous (15 ml) solution of sodium borohydride (1.33 g) cooled in an ice water bath over 15 minutes. After the addition, the reaction mixture was stirred at room temperature. 1N hydrochloric acid (35 ml) was gradually added to the reaction mixture to degrade excess sodium borohydride, and a 1N aqueous solution of sodium hydroxide (35 ml) was added. This was extracted with ethyl acetate (100 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated, and the residue was dried under reduced pressure to give the title compound (1.59 g, 54%) as a pale brown solid.1H-NMR Spectrum (CDCl3) δ (ppm): 2.57 (1H, m), 3.03 (2H, m), 3.24 (2H, m), 3.80 (2H, d, J=5.2 Hz), 4.33 (1H, s), 7.15-7.45 (10H, m).ESI-MS (m/z): 254[M+H]+.
54% (Reference Example F-4) 1-Benzhydryl-3-(hydroxymethyl)azetidine 1-Benzhydryl-3-azetidinecarboxylic acid (3.12 g) was suspended in tetrahydrofuran (60 ml) and cooled under a nitrogen atmosphere in an ice-ethanol bath. Triethylamine (1.96 ml) was added dropwise, and a solution of ethyl chlorocarbonate (1.34 ml) in tetrahydrofuran (5 ml) was added dropwise over 20 min. After the dropwise addition, stirring was carried out at the same temperature for 30 min. The reaction mixture was filtered and washed with tetrahydrofuran (30 ml). The filtrate was added dropwise over 15 min to an aqueous (15 ml) solution of sodium borohydride (1.33 g) cooled in an ice water bath. Upon completion of the dropwise addition, the reaction mixture was stirred at room temperature. To the reaction mixture was gradually added 1N hydrochloric acid (35 ml) to decompose excess sodium borohydride, and a 1N aqueous solution of sodium hydroxide (35 ml) was added. This was extracted with ethyl acetate (100 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated, and the residue was dried under reduced pressure to provide the titled compound as a pale brown solid (1.59 g, 54 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 2.57 (1H, m), 3.03 (2H, m), 3.24 (2H, m), 3.80 (2H, d, J = 5.2 Hz), 4.33 (1H, s), 7.15-7.45 (10H, m). ESI-MS (m/z):254[M+H]+.
54% (Production Example 102) 1-Benzhydryl-3-(hydroxymethyl)azetidine 1-Benzhydryl-3-azetidinecarboxylic acid (3.12 g) was suspended in tetrahydrofuran (60 ml) and cooled under a nitrogen atmosphere in an ice-ethanol bath. Triethylamine (1.96 ml) was added dropwise, and a solution of ethyl chlorocarbonate (1.34 ml) in tetrahydrofuran (5 ml) was added dropwise over 20 min. After the dropwise addition, stirring was carried out at the same temperature for 30 min. The reaction mixture was filtered and washed with tetrahydrofuran (30 ml). The filtrate was added dropwise over 15 min to an aqueous (15 ml) solution of sodium borohydride (1.33 g) cooled in an ice water bath. Upon completion of the dropwise addition, the reaction mixture was stirred at room temperature. To the reaction mixture was gradually added 1N hydrochloric acid (35 ml) to decompose excess sodium borohydride, and a 1N aqueous solution of sodium hydroxide (35 ml) was added. This was extracted with ethyl acetate (100 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated, and the residue was dried under reduced pressure to provide the titled compound as a pale brown solid (1.59 g, 54 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 2.57 (1H, m), 3.03 (2H, m), 3.24 (2H, m), 3.80 (2H, d, J = 5.2 Hz), 4.33 (1H, s), 7.15-7.45 (10H, m). ESI-MS (m/z):254[M+H]+.
65.1. (1 -Benzhydryl-azetidin-3-yl)-methanol: l-Benzhydrylazetane-3-carboxylic acid (101 mg) was dissolved in THF (2 mL) and lithium aluminium hydride (27 mg) was added. The mixture was stirred overnight at RT. Water, sodium potassium tartrate solution and EA were added. The phases were separated, the org. phase was dried (Na2SO4) and evaporated off to afford 93 mg of the desired product. LC-MS (A): tR = 0.67 min; [M+H]+: 254.16.
With lithium aluminium tetrahydride; In tetrahydrofuran;Heating / reflux; A solution of 1-(diphenylmethyl)-3-(hydroxymethyl) azetidine (1 g, 3.9 mmol) [prepared by reduction of 1-(diphenylmethyl)azetidine-3-carboxylic acid (CAS No.: 36476-87-6) using LiAlH4 in refluxing THF] and Et3N (0.71 mL, 5.1 mmol) in THF (30 mL) was treated with methanesulfonyl chloride (0.36 mL, 4.7 mmol) and stirred for 2 h at room temperature. The precipitate was removed by filtration and washed with THF. The liquors were evaporated and the residue partitioned between water and DCM. The DCM layer was separated and the aqueous re-extracted. The combined organics were washed with brine, dried (Na2SO4), filtered and evaporated. The residue was triturated with isohexane, the solid then isolated by filtration and dried to give the title compound as an orange solid (1.1g, 84%). m/z (ES+) 332 (M+H)+.

  • 8
  • [ 36476-86-5 ]
  • [ 36476-87-6 ]
YieldReaction ConditionsOperation in experiment
71.7% Potassium hydroxide (6.48 g) and water (3.25 ml) were added to a solution of 1-benzhydryl-3-cyanoazetidine (5.43 g) in methoxyethanol (54 ml), followed by stirring at 100 C. for 4 hours. The reaction mixture was allowed to cool down to room temperature, and poured into ice. After pH of the mixture was adjusted to 5 with 1N hydrochloric acid, sodium chloride was added thereto. This was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to give a crude product of the title compound as pale yellow crystals. The crystals were suspended by the addition of diethyl ether (15 ml). The crystals were collected by filtration and washed with diethyl ether. This was dried under aeration to give the title compound (4.20 g, 71.7%) as pale yellow crystals.1H-NMR Spectrum (CDCl3) δ (ppm): 3.00-3.90 (5H, m), 4.95 (1H, s), 7.25-7.28 (2H, m), 7.33 (4H, m), 7.53 (4H, m).
71.7% (Reference Example F-3) 1-Benzhydrylazetidine-3-carboxylic acid To a solution of 1-benzhydryl-3-cyanoazetidine (5.43 g) in methoxyethanol (54 ml) were added potassium hydroxide (6.48 g) and water (3.25 ml), followed by stirring at 100 C for 4 hr. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was poured into ice. After adjusting this to pH 5 with 1N hydrochloric acid, sodium chloride was added thereto. This was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer after drying was concentrated under reduced pressure to provide a crude product of the titled compound as pale yellow crystals. The crystals were suspended by addition of diethyl ether (15 ml). The crystals were collected by filtration and washed with diethyl ether. This was dried under aeration to provide the titled compound as pale yellow crystals (4.20 g, 71.7 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 3.00-3.90 (5H, m), 4.95 (1H, s), 7.25-7.28 (2H, m), 7.33 (4H, m), 7.53 (4H, m).
71% A suspension of 1-benzhydryl-azetidine-3-carbonitrile (2.09 g, 8. 42 mmol) in concentrated hydrochloric acid (12 M, 15 mL) was heated at reflux for 30 minutes. The resulting solution was cooled to0 C, and 6 M sodium hydroxide was added until the mixture reached a pH of about 7. The aqueous mixture was <Desc/Clms Page number 112>then extracted with dichloromethane (3 x 150 mL) and dichloromethane: methanol (10: 1,3 x 150 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure to give the title compound (1.60 g, 71 % yield). MS (APCI): m/z 268(M+H)'.
71% A suspension ofl-benzhydryl-azetidine-3-carbonitrile (2.09 g, 8.42 mmol) in concentrated hydrochloric acid (12 M, 15 mL) was heated at reflux for 30 minutes. The resulting solution was cooled to0 C, and 6 M sodium hydroxide was added until the mixture reached a pH of about 7. The aqueous mixture was <Desc/Clms Page number 140>then extracted with dichloromethane (3 x 150 mL) and dichloromethane: methanol (10: 1,3 x 150 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure to give the title compound (1.60 g, 71 % yield). MS (APCI): m/z 268(M+I+.
71.7% (Production Example 83) 1-Benzhydrylazetidine-3-carboxylic acid To a solution of 1-benzhydryl-3-cyanoazetidine (5.43 g) in methoxyethanol (54 ml) were added potassium hydroxide (6.48 g) and water (3.25 ml), followed by stirring at 100 C for 4 hr. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was poured into ice. After adjusting this to pH 5 with 1N hydrochloric acid, sodium chloride was added thereto. This was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer after drying was concentrated under reduced pressure to provide a crude product of the titled compound as pale yellow crystals. The crystals were suspended by addition of diethyl ether (15 ml). The crystals were collected by filtration and washed with diethyl ether. This was dried under aeration to provide the titled compound as pale yellow crystals (4.20 g, 71.7 %). 1H-NMR Spectrum (CDCl3) δ (ppm): 3.00-3.90 (5H, m), 4.95 (1H, s), 7.25-7.28 (2H, m), 7.33 (4H, m), 7.53 (4H, m).
With potassium hydroxide; In 2-ethoxy-ethanol; water; ethyl acetate; (1-Benzhydrylazetidin-3-yl)carboxylic acid may be prepared by carrying out the procedure in the following manner: a solution of 11 g of potassium hydroxide in 9 cm3 of water is added dropwise to a suspension, cooled to +5 C., of 14 g of (1-benzhydrylazetidin-3-yl)carbonitrile in 140 cm3 of 2-ethoxyethanol and then the mixture is heated to 95 C. After stirring for 16 hours at this temperature, the reaction mixture is poured slowly, with stirring, over ice and left at 0 C. for 68 hours and then concentrated to dryness to dryness at 50 C. under reduced pressure (2.7 kPa). The residue is taken up in 400 cm3 of water, the solution is acidified to pH 4 with 6 N hydrochloric acid and then supplemented with 400 cm3 of ethyl acetate. The resulting suspension is filtered, the solid is drained and then dried at 50 C. under reduced pressure (2.7 kPa). 13.55 g of (1-benzhydrylazetidin-3-yl)carboxylic acid are obtained in the form of a cream-colored solid.
(3) A mixture of the above product (5.79 g), sodium hydroxide (2.57 g) and 50% aqueous ethanol (50 ml) was heated to reflux for 6 hours with stirring. After cooled to 0 C., the mixture was adjusted to pH3 with concentrated hydrochloric acid, and extracted with chloroform. The extract was sequentially washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give 1-diphenylmethylazetidine-3-carboxylic acid (about 6.5 g) as a yellow amorphous solid. The solid was used in the next step without any purification.
In water;Acidic conditions; A solution of diphenylmethanamine (benzhydrylamine) and 2-oxopropane- 1,3 -diyl dimethanesulfonate were reacted to give 1 -benzhydrylazetidin-3-one 10 (Scheme 2). Reduction of the ketone of 10 with a hydride reducing agent gave 1-benzhydrylazetidin-3-ol11. Alternatively, 11 can be prepared by cyclization of benzhydrylamine and epichlorohydrin in diisopropylethylamine and ethanol. Mesylation of with methanesulfonyl chloride gave 1 -benzhydrylazetidin-3 -yl methanesulfonate 12. Displacement of the mesyl group with cyanide ion gave 1 -benzhydrylazetidine-3-carbonitrile 13. Hydrolysis of 13 with aqueous acid gave 1 -benzhydrylazetidine-3-carboxylic acid 14. Deprotection of 14 by hydrogenolysisgave 1 (CAS Reg. No.: 36476-78-5 zwitterion; 102624-46-4 hydrochloride salt; 106887-11-0 sodium salt; 1282041 potassium salt).

  • 9
  • [ 667940-67-2 ]
  • [ 36476-87-6 ]
  • C44H50N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 0℃; The starting material D was prepared according to the following scheme; D To a solution of A (3 g; 6.67 mmol) in DMF (10 ml) were successively added at 0C diisopropylethylamine (1.74 ml; 10 mmol, 1.5 equiv. ), B (2.14 g; 8 mmol, 1.2 equiv. ) and HATU (3.04g ; 8 mmol, 1.2 equiv. ). The mixture was stirred over a week end. After removal of DMF under reduced pressure, a saturated aqueous solution of NaHC03 was added and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over MgS04. The solvent was evaporated and the residue purified by flash chromatography eluting with 80/20 ethyl acetate/petroleum ether to give C (4.1 g). Yield: 88%
  • 10
  • [ 36476-87-6 ]
  • 1-Diphenylmethyl-3-(N-[2-hydroxyethyl]-N-methylcarbamoyl)azetidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Preparations 62 to 64 The compounds of the following tabulated Preparations of the general formula: STR428 were prepared by a similar procedure to that of Preparation 59 using <strong>[36476-87-6]1-diphenylmethylazetidine-3-carboxylic acid</strong> and the appropriate amine as starting materials.
  • 11
  • [ 53871-06-0 ]
  • [ 36476-87-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In tetrahydrofuran; methanol; PREPARATION 12-1) To a solution of 1-(diphenylmethyl)-3-methoxycarbonylazetidine (28 g) in methanol (270 ml) and tetrahydrofuran (130 ml) was added 1N sodium hydroxide (115 ml) and the solution was stirred at room temperature for 1.5 hours. The solution was then concentrated to remove organic solvents under reduced pressure. The resultant aqueous solution was adjusted to pH 2.95 with 10% hydrochloric acid, and resulting precipitates were collected by filtration, washed with water and dried to give 1-(diphenylmethyl)-3-carboxyazetidine (24.7 g). mp: 138-140 C. NMR (DMSO-d6, δ): 3.09-3.45 (5H, m), 4.42 (1H, s), 7.13-7.43 (10H, m).
  • 12
  • [ 557-66-4 ]
  • [ 36476-87-6 ]
  • [ 530-62-1 ]
  • [ 91189-21-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In chloroform; acetonitrile; 1-(Diphenylmethyl)-N-ethyl-3-azetidinecarboxamide To a solution of 7.5 g (28 mmole) of 1-(diphenylmethyl)azetidine-3-carboxylic acid in 75 ml of acetonitrile was added 6.0 g (37 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated at 60 C. for two hours and successively treated with 3.1 g (30.8 mmole) of triethylamine and 2.52 g (30.8 mmole) of ethylamine hydrochloride. The reaction was stirred at 60 C. for an additional hour, the solvent evaporated in vacuo and the residue dissolved in chloroform. After washing with water and drying over magnesium sulfate, the chloroform layer was evaporated in vacuo to give 9.4 g of 1-(diphenylmethyl)-N-ethyl-3-azetidinecarboxamide, mp 91-93 C.
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Chemical Structure| 72351-37-2

[ 72351-37-2 ]

1-Benzhydrylazetidine-3-carbaldehyde

Similarity: 0.85

Carboxylic Acids

Chemical Structure| 570423-68-6

[ 570423-68-6 ]

1-(4-Nonylbenzyl)azetidine-3-carboxylic acid

Similarity: 0.88

Chemical Structure| 94985-27-0

[ 94985-27-0 ]

1-Benzylazetidine-3-carboxylic acid

Similarity: 0.87

Chemical Structure| 106014-87-3

[ 106014-87-3 ]

1-Benzylazetidine-3,3-dicarboxylic acid

Similarity: 0.84

Chemical Structure| 889952-36-7

[ 889952-36-7 ]

1-(1-Benzylpiperidin-4-yl)azetidine-3-carboxylic acid

Similarity: 0.83

Related Parent Nucleus of
[ 36476-87-6 ]

Azetidines

Chemical Structure| 53871-06-0

[ 53871-06-0 ]

Methyl 1-benzhydrylazetidine-3-carboxylate

Similarity: 0.90

Chemical Structure| 570423-68-6

[ 570423-68-6 ]

1-(4-Nonylbenzyl)azetidine-3-carboxylic acid

Similarity: 0.88

Chemical Structure| 94985-27-0

[ 94985-27-0 ]

1-Benzylazetidine-3-carboxylic acid

Similarity: 0.87

Chemical Structure| 887591-82-4

[ 887591-82-4 ]

Ethyl 1-benzhydrylazetidine-3-carboxylate

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Chemical Structure| 72351-37-2

[ 72351-37-2 ]

1-Benzhydrylazetidine-3-carbaldehyde

Similarity: 0.85

; ;