Hydroxylamine → 4-(4-Fluoro-phenyl)-N-hydroxy-4-methylsulfanyl-butyramide

Participants

Reaction Steps

To a solution of methyl 4-(4-fluorophenyl)-4-(methylthio)butanoate (30.0 mg, 0.12 mmol) dissolved in 2 mL of THF, methanol, and 50 wt % NH2OH in H2O (2:2:1) was added KCN (4.0 mg, 0.06) and the resulting mixture stirred for 3 days at room temperature. The reaction was quenched by the addition of aqueous 1M HCl (10 mL) and the resulting mixture extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×5 mL). The product was isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to give the title compound (27 mg) as a colorless oil.

Provenance & Evidence