Hydrochloric Acid → 7alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

反応式

[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]4)[C@H:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=O)[CH2:5][C:4]=2[CH:3]=1.B.Cl>O1CCCC1>[CH3:32][NH:31][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:6]1[CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:19]=[CH:18][C:17]=2[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]1

参加物

実験手順

A mixture of 9-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methylnonanamide (Example 27; 0.047 g.) and a molar solution of borane in tetrahydrofuran (5 ml.) was heated under reflux for 2 hours, cooled and concentrated aqueous hydrochloric acid (2 ml.) was added. The tetrahydrofuran was removed by evaporation and the residue was basified with aqueous 5N-sodium hydroxide solution and extracted three times with ethyl acetate (10 ml. each time). The combined extracts were washed with water (2 ml.), dried and evaporated to dryness. There was thus obtained as an oil 7α-(9-methylaminononyl)oestra-1,3,5(10)-triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.