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
