167357-55-3|(S)-2-((Benzyloxy)methyl)morpholine| Ambeed

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CAS No. :	167357-55-3
Formula :	C₁₂H₁₇NO₂
M.W :	207.27
SMILES Code :	[C@@H]1(COCC2=CC=CC=C2)CNCCO1

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

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) .

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Disposal
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CAS No.: 167357-55-3

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CAS No.: 167357-55-3

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[ 167357-55-3 ] Synthesis Path-Downstream 1~2

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed