Synthesis
Step 1: D-cyclohexylglycine (1 g, 6.36 mmol) was added batchwise to a stirred suspension of anhydrous tetrahydrofuran (THF, 20 mL) of lithium aluminum hydride (LiAlH4, 724 mg, 19.08 mmol) at room temperature. The reaction mixture was heated to 80 °C and kept for 4 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and then water (1 mL), 1 M aqueous sodium hydroxide (NaOH) (1 mL) and water (3 mL) were added slowly in sequence to quench the reaction. The mixture was filtered and the filtrate was extracted by partitioning with dichloromethane (DCM), 1 M aqueous NaOH and saturated aqueous sodium potassium tartrate. The organic phase was separated and further washed with 1 M NaOH aqueous solution. The organic phase was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the crude product (R)-2-amino-2-cyclohexylethanol (400 mg) without further purification. It was detected by liquid chromatography-mass spectrometry (LCMS, ESI) at m/z 144 ([M + H]+).
References
[1] Chemische Berichte, 1986, vol. 119, # 7, p. 2191 - 2207
[2] Journal of Organic Chemistry, 1983, vol. 48, # 13, p. 2195 - 2202
[3] Patent: EP2766359, 2016, B1. Location in patent: Paragraph 0536
