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[ CAS No. 121282-70-0 ] {[proInfo.proName]}

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Chemical Structure| 121282-70-0
Chemical Structure| 121282-70-0
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Product Details of [ 121282-70-0 ]

CAS No. :121282-70-0 MDL No. :MFCD04974283
Formula : C11H21NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :XVROWZPERFUOCE-RKDXNWHRSA-N
M.W : 215.29 Pubchem ID :10921888
Synonyms :

Safety of [ 121282-70-0 ]

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

Application In Synthesis of [ 121282-70-0 ]

* 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 [ 121282-70-0 ]

[ 121282-70-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 24424-99-5 ]
  • [ 931-15-7 ]
  • [ 121282-70-0 ]
YieldReaction ConditionsOperation in experiment
96.29% With triethylamine; In dichloromethane; at 0 - 25℃; for 16h; To a solution of compound 1 (10.00 g, 86.83 mmol) and di-tert-butyl dicarbonate (20.85 g, 95.51 mmol, 21.95 mL) in DCM (100.00 mL) was added TEA (26.36 g, 260.49 mmol, 36.11 mL) at 0 C. The mixture was stirred at 25 C for 16 hr. TLC showed the reaction was completed. The resulting mixture was diluted with DCM (100 mL) and washed with water (60 mL*3). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford the crude. The crude was purified by column (Petroleum ether: Ethyl acetate = 25:1, 10:1, 5:1). Compound 2 (18.00 g, 96.29% yield) was obtained as a white solid. ?H NIVIR (400 IVIHz, CHLOROFORM-d): = 4.69 - 4.18 (m, 1H), 3.22 (br d, J=5.7 Hz, 2H), 2.05 - 1.82 (m, 2H), 1.71 - 1.58 (m, 2H), 1.38 (s, 9H), 1.30 - 0.97 (m, 4H). TLC (Petroleum ether: Ethyl acetate =3:1) Rf= 0.23.
With triethylamine; at 0 - 20℃;Large scale; Deprotection was carried out in 4 batches and a total of 8262.0 g (96.1 %) was isolated. The following yields and purities were obtained for each batch: j0114j 20% Palladium hydroxide (201.7 g) was charged to a pressure vessel as a slurry in MeOH (2 L). Stage 3 (2017 g) was then charged as a solution in MeOH (13 L). The mixture was stirred under H2 (40 psi) at room temperature until TLC (thin layer chromatography) analysis indicated complete consumption of the starting material. The mixture was filtered through an in-line filter and the vessel was washed with MeOH (6 L). The filtrates were transferred to a 50 L vessel and cooled to 0 C. Triethylamine (1371 mL) was added, followed by di-t-butyl dicarbonate (2256 mL), keeping the internal temperature <15 C. When the addition was complete the mixture was stirred at room temperature until TLC indicated complete consumption of the amine intermediate. The reaction mixture was evaporated and the resulting off-white solid was dissolved in DCM (16 L). The solution was washed with H20 (2 x 8 L) and brine (8 L), dried over anhydrous Na2504, filtered, evaporated and dried in a vacuum oven at 40 C.
  • 2
  • [ 121282-70-0 ]
  • [ 145106-47-4 ]
YieldReaction ConditionsOperation in experiment
47 g In dichloromethane; at 0 - 25℃; for 1h; To a solution of compound 2 (48.00 g, 222.96 mmol) in DCM (500.00 mL) was added DMP (104.02 g, 245.26 mmol) at 0 C. The mixture was stirred at 025 C for 1 hr. TLC showed the reaction was completed. The reaction was quenched with sat. Na2SO3 aq. and sat. NaHCO3 aq. (V/V = 2:3, 1000 mL), extracted with DCM (100 mL*3). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to afford a crude, which was purified by column chromatography on silica gel (Petroleum ether: Ethyl acetate = 25:1, 15:1) to afford compound 3 as a colorless oil (47.00 g). TLC (Petroleum ether: Ethyl acetate = 3:1)Rf= 0.69.
  • 3
  • [ 108-05-4 ]
  • [ 121282-70-0 ]
  • [ 121282-70-0 ]
  • (1R,2R)-1-acetoxy-2-tert-butoxycarbonylamino-cyclohexane [ No CAS ]
  • 4
  • [ 121282-70-0 ]
  • [ 121282-70-0 ]
  • (1R,2R)-1-acetoxy-2-tert-butoxycarbonylamino-cyclohexane [ No CAS ]
  • 5
  • [ 121282-70-0 ]
  • [ 931-15-7 ]
  • 6
  • [ 124-63-0 ]
  • [ 121282-70-0 ]
  • [ 365996-28-7 ]
YieldReaction ConditionsOperation in experiment
64% With pyridine; In dichloromethane; at 0 - 20℃; for 3.5h; Pyridine (25.0 mL) was added to a solution of cyclohexanol 397c in 300 mL of dry dichloromethane at 0 C. Methanesulfonyl chloride (8.0 mL) in 100 mL of dry dichloromethane was added over 15 min. The reaction mixture turned to a homogeneous yellow solution. The reaction mixture was stirred at 0 C for 15 min and then the cooling bath was removed. Reaction was stirred at room temp for about 3 h. The mixture was partitioned between ether (500 mL) and aqueous 1 N HCI (100 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (100 mL), brine (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel (gradient: ethyl acetate/ (hexanes- dichloromethane, 1: 1); 0: 10 to 2: 8) to afford the product 397d (9.7 g; 64 %) as a white solid.
In pyridine; diethyl ether; [Referential Example 45] (1S,2S)-1-tert-Butoxycarbonylamino-2-methanesulfonyloxy-cyclohexane: <strong>[121282-70-0](1S,2S)-2-tert-Butoxycarbonylamino-1-cyclohexanol</strong> (646 mg) was dissolved in pyridine (4 ml), methanesulfonyl chloride (378 mg) was added with ice cooling, and the mixture was stirred for 5 hours. After diethyl ether was added to the reaction mixture and washed 5 times with water, the resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (630 mg) as colorless crystals. mp 123-124C. [alpha]D+7.16 (19.8C, C=1.01, CHCl3). 1H-NMR (CDCl3) delta: 1.20-1.40(3H,m), 1.44(9H,s), 1.55-1.70(2H,m), 1.70-1.80(1H,m), 2.03-2.23(2H,m), 3.03(3H,s), 3.58(1H,br.s), 4.44(1H,td,J=9.8,4.2Hz), 4.67(1H,br.s).
The synthesis of the mesylate was carried out in 3 batches and a total of 10890.6 g was isolated. The following yields and purities were obtained for each batch: (1S,2S) tert-Butyl (1 S,2 S)-2-hydroxycyclohexylcarbamate (2480 g) was dissolved in DCM (24.8 L) and the solution was cooled to <5 C. Triethylamine (4022 mL) was added over 10 mm, followed by methanesulfonyl chloride (1343 mL) over 1 h. When the addition was complete, the mixture was stirred at room temperature for 1 h. TLC analysis indicated complete consumption of the starting material. Water (9073 mL) was charged to the mixture, which was then stirred at room temperature for 10 mm. The layers were separated and the organic layer was washed with water (9073 mL), dried over MgSO4, filtered and evaporated. The resulting solid was azeotroped with EtOAc (3000 mL) and heptane (3000 mL) then dried in a vacuum oven at 40 C.
  • 7
  • [ 24424-99-5 ]
  • [ 119479-49-1 ]
  • [ 121282-70-0 ]
  • 8
  • [ 764659-69-0 ]
  • [ 121282-70-0 ]
YieldReaction ConditionsOperation in experiment
100% With ethanol;palladium on activated charcoal; In cyclohexene; for 6h;Heating / reflux; The product from Part A (8.0 g, 26.2 mmol) was dissolved in cyclohexene (100 mL) and ethanol (150 mL), and Pd/C (2.0 g) was added. The reaction mixture was refluxed for 6 h and filtered through a pad OF CELITENo.. The filtrate was evaporated to afford (1S, 2S)-2-hydroxy-cyclohexyl-carbamic acid tert- butyl ester (5.7 g, 100%) as a white solid. MS M/Z 216.2 ([M+H]+).
99% With hydrogen;palladium(II) hydroxide/carbon; In methanol; under 2068.65 Torr; 20% palladium dihydroxide on carbon (30 mol% ; 10.8 g) was added to a solution of benzyl ether 397b (15.7 g) in 300 mL of methanol. The heterogeneous mixture was subjected to hydrogenation at 40 psi until no more starting material was detected by TLC (ethyl acetate/hexanes; 2: 8). The mixture was filtered thru celite and the filtrate was concentrated under reduced pressure. No further purification was carried out for the product 397c (11.1 g; 99%).
  • 10
  • [ 121282-70-0 ]
  • [ 365996-26-5 ]
  • 11
  • [ 121282-70-0 ]
  • (1S,2R)-N1-[(5-Chloroindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine [ No CAS ]
  • 12
  • [ 121282-70-0 ]
  • [ 365996-31-2 ]
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