Triethylamine → Methanesulfonic acid 9-(4-methanesulfonyloxy-phenyl)-2-(3-methanesulfonyloxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-yl ester

Participants

Reaction Steps

Combine 9-(4-Hydroxy-phenyl)-2-(3-hydroxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol (0.1 g, 0.284 mmol), methanesulfonyl chloride (0.11 g, 0.94 mmol), triethylamine (0.19 g, 1.9 mmol), 2,6-dimethylaminopyridine (0.02 g, cat.) and methylene chloride (5 ml) and stir 15 hours. Remove solvent in vacuo and add ethyl acetate and water. Wash 1× with sodium bicarbonate solution solution followed by water. Dry over anhydrous sodium sulfate and remove solvent in vacuo to yield preparation 133 (0.16 g, g, 96%). 1H NMR (CDCl3): 7.34 (d, J=8.8 Hz, 2H), 7.28 (d, J=8 Hz, 2H), 7.26 (s, 1H), 7.09 (s, 1H), 4.28 (t, J=7.1 and 6.2 Hz, 2H), 3.24 (m, 6H), 3.16 (s, 3H), 3.03 (s, 3H), 2.9 (d, J=11.9 Hz, 1H), 2.82 (t, J=7.5 and 8.4 Hz, 3H), 2.45 (d, J=13.7 Hz, 1H), 2.1 (m, 3H), 1.8-1.0 (m, 6H).

Provenance & Evidence