Methyl morpholine oxide → HCID 86762182, compound

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To a solution of 3α-(3-trifluoroacetamidopropylthio)-6-methyleneandrostane-17-one (Prepn. 82, 286 mg) in dry CH3CN (14 mL), NMO (213 mg) and molecular sieves (4 Å, 280 mg) were added followed by the addition of TPAP (10.6 mg). After 1 h at room temperature the mixture was evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 65/35) to give 3α-[(S)-3-trifluoroacetamidopropylsulfinyl]-6-methyleneandrostane-17-one (100 mg, 34% yield). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 9.43 (1H, bb), 4.72 (1H, m), 4.41 (1H, m), 3.24 (3H, m), 2.50-0.86 (24H, m), 0.75 (3H, s), 0.65 (3H, s).

Provenance & Evidence