Hydrochloric Acid → HCID 386752, compound

Participants

Reaction Steps

Under nitrogen, a 20% solution of potassium hydroxide in methanol (15 ml) was added dropwise at room temperature to a suspension of compound 5 (3.0 g, 7.26 mmol) in anhydrous methanol (60 ml). The resulting mixture was stirred at room temperature for 6 hr. The mixture was neutralized with 3 N HCl and the solvent was removed under reduced pressure. The residue was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with brine (2×100 ml), and dried over sodium sulfate. Removal of the solvents provided a white solid 6 (2.34 g, 98%), which was then crystallized from ethyl acetate/hexane to afford title compound 6 as white crystals: mp 197-199° C. (lit. 12 mp 194-196° C.); 1H NMR (CDCl3) δ7.61 (s, 1 H, 4-aromatic CH), 7.20 (s, 1 H, 1-aromatic CH), 4.44 (q, J=6.9 Hz, 2 H, 2-CH2-), 3.83 (t, J=8.5 Hz, 1 H, 17α-H), 2.85-1.40 (m, 20H), 0.97 (s, 3 H, 18-CH3).

Provenance & Evidence