Imidazole → HCID 10740227, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene (Compound 3) (500 mg, 1.329 mmol), imidazole (136 mg, 2.0 mmol) and K2CO3 (551 mg, 3.99 mmol) in dry DMF was heated at about 80° C. under N2 for 2 h. After cooling to room temperature, the reaction mixture was poured onto ice-cold water (100 ml), and the resulting white precipitate was filtered, washed with water, and dried to give a white solid. This was titrated with boiling mixture of hexane/EtOAc to give Compound 9 (520 mg, 92%), mp 218-220° C. 1H NMR (300 MHz, CDCl3): δ 1.08 (6H, s, 18 and 19-Me), 2.04 (3H, s, 3β-OAc), 4.61 (1H, m, 3α-H), 5.42 (1H, d, J=4.8 Hz, 6-H), 7.11 (1H, s, 4'-H), 7.23 (1H, s, 5'-H), 7.63 (1H, s, 2'-H) and 9.74 (1H, s, 16-CHO). Analysis calculated for C25H32O3N2 : C, 73.49; H, 7.90; N, 6.88; Found: C, 73.34; H, 8.05; N, 6.65. HRMS calcd. for C25H32O3N2 408.2413, found 408.2426.

Provenance & Evidence