N-Boc-hexahydro-1H-azepin-4-one → tert-Butyl 4-hydroxyazepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1 g (4.69 mmol) of 4-oxo-azepane-1-carboxylic acid tert-butyl ester), in 2 mL of Methanol and 8 mL of THF, is added at 0° C. (ice bath) sodium tetrahydroborate (0.18 g, 4.69 mmol). The resulting mixture is stirred at 0° C. for 1 h. To the reaction mixture is added at 0° C. (ice bath), a solution of HCl (1N) (2 mL), then solvent is removed and the resulting slurry is diluted with water and extracted with EtOAc (250 mL). The organic layers are combined, dried (Na2SO4), filtered and concentrated to afford the title compound as a colorless oil (0.95 g, 94%). MS (m/e): 216 (M+1).

Provenance & Evidence