反応式
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:8][C@H:7]1[C:19](O)=[O:20])=[O:5])[CH3:2].O>O1CCCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:17])([CH3:16])[CH3:18])([CH3:13])[CH3:14])[CH2:8][C@H:7]1[CH2:19][OH:20])=[O:5])[CH3:2]参加物
4
実験手順
To a cold (ice bath) solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid monoethyl ester (epimeric mixture, 0.7 g) in tetrahydrofuran (3.5 mL) was slowly added a borane complex with tetrahydrofuran (1M, 2.7 mL). The resulting solution was stirred for 3 h in the ice bath then slowly poured into water. The mixture was extracted with diethylether. The combined organic layers were washed with brine and dried over sodium sulfate then concentrated in vacuo. The residue was purified by flash chromatography on silica gel with cyclohexane/ethylacetate (6:1 v/v) as eluant to afford the title compound (0.49 g, 73%) as light yellow oil. MS (EI): 303.2 (M+H)+.
後処理
- extractionThe mixture was extracted with diethylether
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationthen concentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel with cyclohexane/ethylacetate (6:1 v/v) as eluant
出典と根拠
- ORDレコード
- ord-ff4d2bb326124cd0ad71cd2a15c4d7ba
- 出典データセット
- uspto-grants-2011_02
- 特許番号
- US07893099B2
関連ノート
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