Borane;tetrahydrofuran → (7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepane monohydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of (7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepan-3-one (535 mg) in THF (10 ml) was added 1 M borane-THF solution (5 ml), and the mixture was stirred at 70° C. for 30 min. The reaction mixture was quenched with water, 2N hydrochloric acid (5 mL) was added, and the mixture was stirred at 70° C. for 10 min. The solvent was evaporated under reduced pressure, the residue was alkalified with potassium hydroxide, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (NH, eluent; hexane:ethyl acetate (1:1)-(0:10)) to give the title compound as a free amine form (397 mg).

Provenance & Evidence