Hydroxyamine hydrochloride → HCID 86759351, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3,17,β-diacetoxy-2-ethoxy-estra-1,3,5(10)-triene-6-one (5, 800 mg, 1.93 mmol) in pyridine (12 ml) was treated with hydroxylamine hydrochloride (1.07 g, 15.4 mmol). The resulting mixture was stirred and heated at 100° C. for 30 min. The mixture was cooled to room temperature and then poured into ice/water mixture (150 ml). The compound was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with sodium bicarbonate (100 ml), water (2×100 ml) and brine (2×100 ml), dried over sodium sulfate, and evaporated to dryness. Chromatography of the residue on silica gel using 30% ethyl acetate in hexane gave the title compound (763 mg, 89%), which was crystallized from ethyl acetate/hexane to afford title compound 27 as yellowish crystals: mp 226-227° C. 1H NMR (CDCl3) δ7.55 (s, 1 H). 6.78 (s, 1 H), 4.75 (t, J=8.5 Hz, 1 H), 4.19 (q, J=6.9 Hz, 2 H), 3.15 (dd, J=4.3 and 12 Hz, 1 H), 1.2-2.40 (m, 18 H), 0.85 (s, 3 H); CIMS (isobutane) m/z (rel intensity) 388 (MH+, 100), 372 (MH—H2O, 10), 328 (75); Anal. Calcd for C22H29O5N: C, 68.20; H, 7.54; N, 3.61. Found: C, 68.04; H, 7.62; N, 3.54.

Provenance & Evidence