| Identification | Back Directory | [Name]
(S)-2-Methyl-morpholine | [CAS]
74572-13-7 | [Synonyms]
(S)-2-Methyl-morpholine
(2S)-2-MethylMorpholine
(S)-2-Methylmorpholine HCl
Morpholine, 2-Methyl-, (S)-
Morpholine, 2-methyl-, (2S)- | [Molecular Formula]
C5H11NO | [MDL Number]
MFCD11041199 | [MOL File]
74572-13-7.mol | [Molecular Weight]
101.15 |
| Chemical Properties | Back Directory | [Boiling point ]
137℃ | [density ]
0.891 | [Fp ]
41℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
9.01±0.40(Predicted) | [Appearance]
Colorless to light yellow Liquid | [Optical Rotation]
Consistent with structure |
| Hazard Information | Back Directory | [Uses]
(S)-2-Methylmorpholine is a reactant in the synthesis of imidazo[1,2-a]-pyrimidin-5(1H)-ones as PI3K-beta selective inhibitors. | [Synthesis]
General procedure for the synthesis of (S)-2-methylmorpholine from the compound (CAS: 74572-10-4): (2S)-2-methyl-4-(4-methylphenyl)sulfonylmorpholine (EE2, 13.26 g, 51.93 mmol), phenol (9.77 g, 103.86 mmol), and an acetic acid solution of 33% HBr (89 mL, 363.52 mmol) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was evaporated to dryness. The crude product obtained was ground with ether (Et2O) to form a solid, which was collected by filtration and dried under vacuum to afford (2S)-2-methylmorpholine hydrobromide (6.77 g, 72% yield) as a white solid.1H NMR (400 MHz, DMSO) δ 1.18 (3H, d), 2.74 (1H, t), 3.01 (1H, td) 3.23 (1H, d), 3.26 (1H, d), 3.73 (1H, td), 3.79 (1H, dqd), 3.98 (1H, dd), 8.86 (2H, s). | [References]
[1] Patent: WO2010/136778, 2010, A1. Location in patent: Page/Page column 85
[2] Tetrahedron, 1980, vol. 36, p. 409 - 415 |
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