Hydrochloric Acid → HCID 178523816, compound

Participants

Reaction Conditions

Reaction Steps

This ketone (2.36 g, 9.55 mmol) in THF (5 mL) was added dropwise to a stirred solution of L-selectride in THF (1M, 19.1 mL, 9.55 mmol) under N2 at -78° C. The reaction mixture was stirred at -78° C. for 3 hours, methanol (0.5 mL) was added, and the reaction mixture was allowed to warm to room temperature. 1N hydrochloric acid (5 mL) was added and the mixture stirred overnight. The reaction mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with brine (2×20 mL), dried over anhydrous sodium sulfate, filtered, and the solvent removed in vacuo to yield 2.73 g crude oil. The crude product was purified by MPLC on silica gel (70-230 mesh, 1.5×45 cm column) using a 1:1 hexane/ethyl acetate, 2:1 hexane/ethyl acetate, and ethyl acetate step gradient. Fractions containing pure product were pooled and concentrated in vacuo to give a clear oil (cis-N-Cbz-4-aminocyclohexanol) (1.35 g, 57% yield): 1H NMR (300 MHz) δ 7.35 (m, 5H), 5.10 (s, 2H), 4.74 (br, 1H), 3.91 (br, 1H), 3.62 (br, 1H), 1.18 (m, 8H); MS: (M+H)+ =250, (M+H+NH3)+ =267.

Provenance & Evidence