(Dimethyl sulfide)trihydroboron → rel-1,1-Dimethylethyl N-[(1R,3R)-3-(hydroxymethyl)cyclohexyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Racemic trans 3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1 g, 4.11 mmol) was dissolved in THF (30 mL) and borane dimethylsulfide 2M in THF (3 mL, 6 mmol) was added slowly. The resulting colorless solution was stirred at 40° C. After 4 hours the reaction mixture was cooled to 0° C., quenched by addition of saturated aqueous NaHCO3, and extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and evaporated to give 0.905 g of crude racemic trans 3-hydroxymethyl-cyclohexyl-carbamic acid tert-butyl ester as a colorless oil (>95% yield).

Provenance & Evidence