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

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.

1. customThe reaction was quenched by the addition of aqueous 1M HCl (10 mL)
2. extractionthe resulting mixture extracted with ethyl acetate (3×10 mL)
3. washThe combined organic layers were washed with brine (2×5 mL)
4. customThe product was isolated by flash column chromatography
5. washeluting with 0% to 10% methanol/DCM

ORD record

ord-aa7a5e251ad44263a0d233d339f23eb7

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119692B2