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CAS No. : | 2930-05-4 | MDL No. : | MFCD00068664 |
Formula : | C10H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QNYBOILAKBSWFG-UHFFFAOYSA-N |
M.W : | 164.20 | Pubchem ID : | 94247 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium azide; at 80℃; for 10h;Green chemistry; | General procedure: An equimolar mixture of epoxides 1 and NaN3 wasstirred for 10 min in 1 g of IL i.e. [bmim]Br, loaded withCu(I) at 5 mol% w.r.t. reactant concentration. To theresultant, were added an equimolar ratio of terminalalkynes 2 via a syringe and the reaction was furthermaintained under stirring at 80 8C for a specified period oftime. After completion of the reaction (as indicated byTLC), 10 mL of distilled water were added under continuousstirring, and solid crude product obtained was simplycollected by filtration. Purification of crude products wascarried out by recrystallization from ethanol. The filtratecontaining IL and the Cu(I) catalyst was immediatelyreduced under low pressure and further dried at 100 8C for20-30 min in a hot air oven, for the consecutive reactionruns. Physical data of some representative compounds aregiven below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In methanol; | a) 199 g of 2-aminoethyl hydrogen sulfate are added to 164 ml of 70percent sodium hydroxide solution, the solution is heated to 50° C. and added dropwise to a solution of (RS)-benzyloxymethyloxirane in 280 ml of methanol. After 1 hour at 50° C. a further 280 ml of 70percent sodium hydroxide solution are added thereto and the solution is stirred overnight. Then, the reaction mixture is poured on to ice and extracted with toluene. The organic phase is washed with water, dried and evaporated. After distillation there are obtained 26.8 g of rac-2-benzyloxymethylmorpholine, MS: M+ -91=116 (benzyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A (+)-2(S)-(Phenylmethyloxymethyl)morpholine The title compound was obtained (2.33 g, 23percent) from 2-aminoethyl hydrogen sulphate and (-)-2(benzyloxymethyl)oxirane as described in Example 2, Step A. 1 H NMR (360 MHz, CDCl3) delta2.65 (1H, dd, J1 =10, J2 =12 Hz), 2.78-2.93 (3H, m), 3.41 (1H, dd, J1 =5, J2 =10 Hz), 3.48 (1H, dd, J1 =5, J2 =10 Hz), 3.58-3.68 (2H, m), 3.89 (1H, d, J=10 Hz), 4.54 (1H, d, J=12 Hz), 4.56 (1H, d, J=12 Hz), 7.25-7.34 (5H, m), [alpha]27° C.D +2.4° (c=1.0, methanol), MS, CI+, m/z=208 for (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With sodium hydroxide; In methanol; water; at 50 - 55℃; for 17h; | Example 4; (R)-Quinuclidin-3-yl 5-((R)-2-((4-amino-5-chloro-2-methoxybenzamido)methyl)morpholino)hexanoate [Show Image] Mono-(2-amino-ethyl) sulfate (35.2 g, 250 mmol) was dissolved in 60 mL of aqueous sodium hydroxide solution (40percent) with stirring. The solution of (S)-benzyl glycidyl ether 4a (8.2 g, 50 mmol) in methanol was added to the above sodium hydroxide solution. After reacting for 1 hour at 50°C, 100 mL of aqueous sodium hydroxide solution (40percent) was added. The reaction mixture was stirred at 50-55°C for 16 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The resulting mixture was diluted with 100 mL of water and 100 mL of concentrated hydrochloric acid was added dropwise. The mixture was extracted with dichloromethane (500 mL.x.4). The combined organic phase was washed successively with water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (S)-2-benzyloxymethyl-morpholine 4b (5.08 g, yield 49percent) as a yellow liquid. MS m/z (ESI): 208.7[M+1]. 1H NMR (CDCl3, 400 MHz) delta 7.4-7.2(m, 5H), 4.56 (s, 2H), 3.9 (d, 1H, J=11Hz), 3.8-3.35 (m, 4H), 2.92 (dd, 1H, J1=2.5Hz, J2=12.0Hz), 2.85-2.75 (m, 2H), 2.66 (dd, 1H, J1=10.5Hz, J2=12.0Hz), 2.4 (s, 1H). |
49% | With sodium hydroxide; In methanol; water; at 50 - 55℃; for 17h; | Mono-(2-amino-ethyl) sulfate (35.2 g, 250 mmol) was dissolved in 60 mL of aqueous sodium hydroxide solution (40percent) with stirring. The solution of (S)-benzyl glycidyl ether 4a (8.2 g, 50 mmol) in methanol was added to the above sodium hydroxide solution. After reacting for 1 hour at 50° C., 100 mL of aqueous sodium hydroxide solution (40percent) was added. The reaction mixture was stirred at 50-55° C. for 16 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The resulting mixture was diluted with 100 mL of water and 100 mL of concentrated hydrochloric acid was added dropwise. The mixture was extracted with dichloromethane (500 mL.x.4). The combined organic phase was washed successively with water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (S)-2-benzyloxymethyl-morpholine 4b (5.08 g, yield 49percent) as a yellow liquid.MS m/z (ESI): 208.7 [M+1].1H NMR (CDCl3, 400 MHz) delta 7.4-7.2 (m, 5H), 4.56 (s, 2H), 3.9 (d, 1H, J=11 Hz), 3.8-3.35 (m, 4H), 2.92 (dd, 1H, J1=2.5 Hz, J2=12.0 Hz), 2.85-2.75 (m, 2H), 2.66 (dd, 1H, J1=10.5 Hz, J2=12.0 Hz), 2.4 (s, 1H). |
In a 500 mL flask were combined (S)-benzyl glycidyl ether (15g, 91.4 rniriol) , MeOH (10 mL) , and 50percent wt. NaOH (30 mL, 365 mmol) . To this mixture was added 2-aminoethylsulfate (25.8 g, 183 mmol) in portions . This heterogeneous mixture was heated to 4O0C at which point the solution becomes homogenous. The temperature was maintained at 400C for 4 h. The reaction was cooled slightly and additional solid NaOH (14.6 g, 365 mmol) was added along with 50 mL toluene. The biphasic solution then was heated to 65°C for 12 h. The reaction was cooled to room temperature, the layers were separated and the aqueous layer was extracted once with EPO <DP n="76"/>75 mli of toluene. The combined organic layers were washed three times with 75 mL portions of IM HCl . The pH of the combined aqueous layers was adjusted to pH 12 with . aqueous NaOH solution and extracted four times with 70 mL portions of EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo to yield 10.084 g of the desired morpholine as an opaque oil.The crude morpholine product was dissolved in CH2Cl2 (100 mL) and TEA (12.1 mL, 87.5 mmol) and di-tert- butyl dicarbonate (15.9 g, 73 mmol) was added accompanied by the generation of CO2 gas. The reaction was stirred at room temperature for 18 h, then quenched with 35 mL sat'd aqueous NaHCO3 solution. An additional 50 mL water was added and the layers were separated. The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography (20percent EtOAc/hexane) to give the desired N-Boc-O-benzyl morpholine as a pale yellow oil (5.536 g) .The purified diprotected morpholine was dissolved in 50 L absolute EtOH and Pd(OH)2 (1.26 g, 20percentwt, 1.8 mmol) was added. A hydrogen balloon was attached and the flask was evacuated using an aspirator and backfilled with H2 three times. The reaction was stirred under H2 for 30 h. The mixture was filtered over celite, rinsing the celite pad thoroughly with EtOH. The filtered solution was concentrated down under vacuum to yield of the desired N-boc-morpholine alcohol as a pale white solid (3.918 g) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; at 50℃; for 1h; | Step a) 2R-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester2g of S-(+)-2-(benzyloxymethyl)-oxirane and 7 g of 2-aminoethyl hydrogen sulfate were weighed into a 100 ml round bottle flask, 2 g of NaOH dissolved in H2O was added and the stirred mixture was heated at 50 0C for 1 hour. 4 g of NaOH dissolved in 10 ml H2O, solution was added to the stirred mixture, which was then heated at 55 0C for 16 h. After cooling the mixture to room temperature, it was diluted with 100 ml H2O and 100 ml dioxane and 2.66 g of di-tert-butyl dicarbonate was added. The mixture was stirred at room temperature for 5 hours, transferred into a separation funnel and extracted with 2 x 75 ml of toluene. Combined organic phases were washed with 2 x 50 ml of 1 M citric acid (aq.), once with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified on silica yielding 2R- Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester 1.85 g (49percent) as a clear oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; at 50℃; for 1h; | 3g of R-(+)-2-(benzyloxymethyl)-oxirane and 10.5 g of 2-aminomethyl hydrogen sulfate were weight in a 100 ml round bottle flask, 3 g of NaOH dissolved in H2O was added and the stirred mixture was heated at +50 0C for 1 hour. 6 g NaOH was dissolved in 10 ml H2O, solution was added to the stirred mixture, which was then heated at + 550C for 72 h. After cooling the mixture to room temperature, it was diluted with 100 ml H2O and 100 ml dioxane and 4.0 g of di-tert-butyl dicarbonate was added. The mixture was stirred at room temperature for 5 hours, transferred into a separation funnel and extracted with 2x75 ml of toluene. Combined organic phases were washed with 2 x 50 ml of 1 M citric acid (aq.), once with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified on silica yielding 2S-Benzyloxymethyl-morpholine-4- carboxylic acid tert-butyl ester 2.55 g (45percent) as a clear oil. |
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