Carbamic acid, [(1S,2R)-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester (9CI)

1269650-09-0

214679-17-1

To a stirred solution of (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 5.35 mmol) in tetrahydrofuran (THF, 50 mL) was slowly added an aqueous solution of 1N lithium hydroxide (LiOH, 9.63 mL, 9.63 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 6 hours. After completion of the reaction, the mixture was partitioned between ethyl acetate (EtOAc) and water. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:1) to afford the target product (1S,2R)-tert-butyl 2-hydroxycyclohexylcarbamate (1.15 g, 100% yield).