Water → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester

HRID 1367486

반응식

HRID 1367486 반응식
[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]

참가 물질

4

반응물 2

HCID 962WaterHCID 59619299(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid monoethyl ester

생성물 1

HCID 59619451(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester수율 73.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ff4d2bb326124cd0ad71cd2a15c4d7ba
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

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