Hydrochloric Acid → tert-Butyl 4-hydroxyazepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-oxo-azepane-1-carboxylic acid tert-butyl ester (13.6 g, 63.8 mmol) in methanol (10 mL) and tetrahydrofuran (30 mL) at 0° C. is added lithium borohydride (1.40 g, 63.8 mmol). The mixture is stirred at 0° C. for 60 minutes. Hydrochloric acid (1.0 M, 40 mL) is added. The mixture is concentrated under reduced pressure and extracted with ethyl acetate (2×). The combined ethyl acetate layers are dried (Na2SO4) and concentrated to a residue. The residue is purified on silica using a gradient of ethyl acetate in hexanes (40 to 80%) to yield the title compound (13.6 g, 99.1%).

Provenance & Evidence