Formaldehyde → benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate

Participants

Reaction Steps

A solution of benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)carbamate (300 mg, 0.73 mmol) in acetonitrile (4 mL) was treated with formaldehyde (37% aqueous, 300 μL), sodium cyanoborohydride (138 mg, 2.19 mmol) and a few drops of acetic acid. After stirring at room temperature, the mixture was treated with aqueous sodium hydroxide (1.0 N) and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography, eluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonia, to provide a gum (280 mg, 90%).

Provenance & Evidence