反应详情

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)+.

1. extractionThe mixture was extracted with diethylether
2. washThe combined organic layers were washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationthen concentrated in vacuo
5. customThe residue was purified by flash chromatography on silica gel with cyclohexane/ethylacetate (6:1 v/v) as eluant