ChemicalBook--->CAS DataBase List--->914299-79-9

914299-79-9

914299-79-9 Structure

914299-79-9 Structure
IdentificationBack Directory
[Name]

(S)-3-phenylmorpholine
[CAS]

914299-79-9
[Synonyms]

(S)-3-phenylmorpholine
(S)-4-Phenylmorpholine
(3S)-3-phenylmorpholine
Morpholine, 3-phenyl-, (3S)-
[Molecular Formula]

C10H13NO
[MDL Number]

MFCD11016232
[MOL File]

914299-79-9.mol
[Molecular Weight]

163.22
Chemical PropertiesBack Directory
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[Appearance]

Off-white to light yellow Solid
[Optical Rotation]

44.9069°(C=1.0038g/ml MEOH)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

(S)-3-phenylmorpholine(914299-79-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

(5S)-5-Phenyl-3-morpholinone

1052209-96-7

(S)-3-phenylmorpholine

914299-79-9

Step 3. A THF solution of (S)-5-phenylmorpholin-3-one (481 mg, dissolved in 6 mL of THF) was slowly added dropwise to a LiAlH4/THF suspension (0.47 g LiAlH4 dissolved in 2 mL of THF) at room temperature for a controlled time of over 5 minutes. After the dropwise addition, the reaction mixture was stirred at room temperature for 1 h, followed by transferring to a 72 °C oil bath for heating overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by sequential addition of H2O (0.47 mL), 3M NaOH aqueous solution (0.47 mL) and H2O (1.4 mL). The quenched mixture was diluted with Et2O (30 mL) and stirred for 10 min before separating the ether phase by filtration. The filtrate was concentrated and further dried under vacuum to give (S)-3-phenylmorpholine as a colorless solid (424 mg, 96% yield).LCMS (m/z): 164.2 (MH+), retention time 0.33 min.

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4316 - 4320
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5319 - 5322
[3] Angew. Chem., 2013, vol. 125, # 20, p. 5427 - 5430,4
[4] Patent: US9242996, 2016, B2. Location in patent: Page/Page column 265; 266
[5] Patent: WO2018/116285, 2018, A1. Location in patent: Page/Page column 24
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