Acetic Acid → HCID 10831118, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Compound 6 (200 mg, 0.590 mmol), hydrazine hydrate (0.57 ml, 1.77 mmol), and acetic acid (0.35 ml) in EtOH (20 ml) was heated at 80° C. while a stream of air was passed through the solution for 6 h. The reaction mixture was concentrated to about 10 ml and after cooling, it was diluted with EtOAc (30 ml) followed by washing with saturated aqueous NaHCO3 (10 ml×2), and brine (10 ml×2), dried (Na2SO4) and concentrated to give a crude product (190 mg). This was purified by FCC (silica gel, CH2Cl2/EtOH, (30:1)) to give the Compound 8 (150 mg, 10-74.6%), mp 246-248° C. 1H NMR (300 MHz, CDCl3): δ 0.56 (3H, s, 18-Me), 1.01 (3H, s, 19-Me), 3.53 (1H, m, 3α-H), 4.19 (1H, t, J 9.6 Hz, 17a-H), 5.37 (1H, d, J=5.2 Hz, 6-H), 7.93 (1H, s, 3′-H) and 8.10 (1H, s, 5′-H). Analysis calculated for C21H31ON3: C, 73.85; H, 9.16; N, 12.31. Found: C, 73.75; H, 9.40; N, 12.28.

Provenance & Evidence