Water → (11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one 3-oxime

Participants

Reaction Steps

Hydroxylamine hydrochloride (20 mg, 0.30 mmol) and water (1 mL) were added to a stirred solution of 100 mg (0.20 mmol) of (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one in dioxane (2 mL). The reaction mixture was stirred overnight at room temperature and then extracted three times with dichloromethane. The combined organic layers were dried through a phase separate filter and evaporated to dryness. Purification of the crude product by HPLC followed by lyophilisation gave (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one 3-oxime as an E/Z mixture (2:1) (85 mg, 0.17 mmol, 84% yield). 1H NMR (400 MHz, CDCl3): δ 0.31 and 0.32 (2×s, in total 3H), 0.83-2.95 (m, 25H), 4.37-4.42 (m, 1H), 5.89 and 6.55 (2×s, in total 1H), 7.26-7.32 (m, 2H), 7.35 (dd, J=8 and 5 Hz, 1H), 7.47-7.51 (m, 2H), 7.86 (dt, J=8 and 1 Hz, 1H), 8.57 (dd, J=5 and 1 Hz, 1H), 8.84 (d, J=1 Hz, 1H).

Provenance & Evidence