Synthesis
General Steps:
Step 1: Tert-butyl (S)-(1-cyclohexyl-3-hydroxypropan-2-yl)carbamate (4.00 g, 15.5 mmol) was dissolved in a mixed solvent of dichloromethane (10 mL) and a dioxane solution of 4N hydrochloric acid (10 mL), and the reaction was stirred for 16 hours at room temperature. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane (40 mL) and subsequently washed with aqueous ammonium hydroxide solution (30 mL). The aqueous layer was then extracted with dichloromethane (40 mL), all organic layers were combined, dried with magnesium sulfate and concentrated to give (S)-2-amino-3-cyclohexyl-1-propanol (2.78 g, 100% yield). Mass spectral analysis showed m/e 158 (M + H)+.
References
[1] Patent: WO2005/14540, 2005, A1. Location in patent: Page/Page column 46
[2] Patent: WO2005/16876, 2005, A2. Location in patent: Page/Page column 35
[3] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 9, p. 2570 - 2572
