Sodium borohydride → [1-Methyl-1-(4-hydroxy-cyclohexyl)-ethyl]carbamic acid tert-butyl ester

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Reaction Steps

2.91 g of [1-Methyl-1-(4-oxo-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester (20) were dissolved in 60 mL of ethanol and 473 mg of sodium borohydride were added at −20° C. The mixture was allowed to warm to room temperature and stirred for 3.5 h. The mixture was evaporated, the residue was dissolved in ethyl acetate and washed twice with 2N hydrochloric acid and once with brine. The organic layer was dried over sodium sulphate and evaporated to dryness to give 2.74 g of (21). Rt=1.27 min (Method 5). Detected mass: 194 (M-Isobutene-H2O+H+).

Provenance & Evidence