Sodium Bicarbonate → (3S,5R,8R,9S,10S,13R,14S,17S)-17-[(E)-methoxyiminomethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diol

Participants

Reaction Steps

To a suspension of 0.16 g of methoxylamine hydrochloride and 0.19 g of NaHCO3 in 12 ml of dioxane and 10 ml of water a solution of 0.50 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 6 ml of dioxane was added dropwise at room temperature. After 15 minutes the solution was diluted with water and extracted with chloroform; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash-chromatography (SiO2) using cyclohexane/ethyl acetate 60/40; the fractions containing the rifle compound were collected and evaporated to dryness. The residue was ground with di-iso-propyl ether/ethanol to give 0.20 g of the title compound (I-aa), as a white solid.

Provenance & Evidence