Sodium borohydride → 5-{3-[(1R,2R,3R,5R)-5-Chloro-2-((E)-3-hydroxy-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propyl}-thiophene-2-carboxylic acid methyl ester
反応式
[BH4-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][C@H:15]2[C@H:19]([Cl:20])[CH2:18][C@@H:17]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C@@H:16]2/[CH:28]=[CH:29]/[C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=1)=[O:6]>CO>[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][C@H:15]2[C@H:19]([Cl:20])[CH2:18][C@@H:17]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C@@H:16]2/[CH:28]=[CH:29]/[CH:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=1)=[O:6]参加物
4
実験手順
NaBH4 (9.2 mg, 0.24 mmol) was added to a solution of ketone 4-3 (59 mg, 0.12 mmol) in methanol (1 mL). The reaction was stirred at room temperature for 2 h and then was quenched by addition of 5 mL 1 M HCl. The resulting mixture was extracted with CH2Cl2 and the combined CH2Cl2 solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/hexanes) gave the title compound (48 mg, 80%).