Water → HCID 86759646, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (7α,14β,17α)-17-(hydroxymethyl)-7-methylestr4-en-3-one (Example 4; 1.0 g) in pyridine (6 ml) was added hydroxylamine hydrochloride (2.65 g). The reaction mixture was stirred at 80° C. for 1.5 h. After cooling, the mixture was poured into water. The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (3E,7α,14β,17α)-3-(hydroxyimino)-7-methylestr-4-ene-17-methanol (0.54 g), [α]D20=+95.5 ° (c=1.41, dioxane), and (3Z,7α,14β,17α)-3-(hydroxyimino)-7-methylestr-4-ene-17-methanol(0.28 g), [α]D20=+87.4 (c=1.0, dioxane).

Provenance & Evidence