Methanol → tert-Butyl 4-hydroxyazepane-1-carboxylate

Participants

Reaction Steps

To a methanol (250 mL) solution of tert-butyl 4-oxoazepane-1-carboxylate (18.1 g, 85.0 mmol) at 0° C. was added sodium borohydride (8.01 g, 212 mmol). The reaction mixture was stirred for 2 hours before concentration in vacuo. The residue was dissolved in dichloromethane (250 mL) and washed with brine. The precipitate was removed by filtration, and the filtrate was dried (magnesium sulfate), filtered and concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3) 3.87 (br s, 1H), 3.49-3.18 (m, 4H), 2.05-1.48 (m, 6H), 1.46 (s, 9H); LC-MS: m/z 238.2 (M+Na).

Provenance & Evidence