Dimethylformamide → (8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

Participants

Reaction Steps

To a stirred solution of 2-ethyl estrone 1 (10.00 g, 33.5 mmol) in anhydrous DMF (100 ml) under inert atmosphere was added potassium carbonate (14.0 g, 100 mmol) followed by Benzyl bromide (4.78 ml, 40 mmol). The reaction was left to stir at r.t. over 2 days. The solid obtained was filtered using a Buchner funnel, dissolved in DCM, filtered to remove any inorganics and concentrated to obtain a white solid. The white solid obtained was re-crystallised with DCM:MeOH (90:10) to obtain the pure product the benzyl ether estrone derivative 2 (12.00 g, 92%) also as a white solid: 1H NMR (270 MHz, CDCl3) δ 0.90 (s, 3H, 18-CH3), 1.17-1.23 (t, J=7.4 Hz, CH2—CH3), 1.51-2.29 (m, 14H), 2.45-2.55 (m, 4H, 16-CH2), 2.62-2.70 (q, J=7.6 Hz, 2H, CH3—CH2), 2.84-2.90 (m, 2H, 6-CH2), 5.04 (s, 2H, CH2-phenyl) 6.64 (s, 4-H), 7.10 (s, 1-CH), 7.28-7.45 (m, 5H); FAB-HRMS calcd for C27H32O2 388.2357 found (M+) 388.2389.

Provenance & Evidence