| Identification | Back Directory | [Name]
3(S)-HYDROXYMETHYLMORPHOLINE | [CAS]
211053-50-8 | [Synonyms]
(3S)-3-Morpholinemethanol
(S)-morpholin-3-ylmethanol
3-Morpholinemethanol, (3S)-
(3S)-morpholin-3-ylmethanol
3(S)-HYDROXYMETHYLMORPHOLINE
(S)-3-Hydroxymethylmorpholine
(3S)-3-Morpholinemethanol,99%e.e. | [Molecular Formula]
C5H11NO2 | [MDL Number]
MFCD06799480 | [MOL File]
211053-50-8.mol | [Molecular Weight]
117.15 |
| Chemical Properties | Back Directory | [Melting point ]
112 °C | [Boiling point ]
218.3±20.0 °C(Predicted) | [density ]
1.045±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
14.85±0.10(Predicted) | [Appearance]
Off-white to brown Solid |
| Hazard Information | Back Directory | [Uses]
(S)-3-Hydroxymethylmorpholine is a chemical reagent used in the synthesis of Aurora kinase inhibitors, used for their anti-tumor activity. Also used in the preparation of human epidermal growth factor receptor 1 & 2 kinase inhbitors in the treatment of solid tumors. | [Synthesis]
To a solution of (S)-(4-benzylmorpholin-3-yl)methanol (10.0 g, 48.3 mmol) in methanol (300 mL) was added 10 wt% of carbon-loaded palladium catalyst (2.0 g), and the reaction mixture was transferred to a Parr reactor. The reaction was carried out for 18 hours at room temperature under hydrogen pressure of 50 psi. Upon completion of the reaction, the mixture was filtered through a Celite pad to remove the catalyst. The filtrate was concentrated under reduced pressure to afford (S)-3-hydroxymethylmorpholine (5.2 g, 92% yield) as a colorless oil.1H NMR (CDCl3) δ: 3.81-3.76 (2H, m), 3.58-3.43 (3H, m), 3.35-3.28 (1H, m), 2.99-2.91 (5H, br.m). Mass spectrum (ES+) m/z: 118.0 ([M + H]+). | [References]
[1] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 41
[2] Patent: WO2009/1089, 2008, A1. Location in patent: Page/Page column 29-30
[3] Patent: WO2009/71895, 2009, A1. Location in patent: Page/Page column 110
[4] Patent: US2011/3785, 2011, A1. Location in patent: Page/Page column 11
[5] Patent: WO2006/114606, 2006, A1. Location in patent: Page/Page column 78 |
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