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

HRID 1367486

Reaction equation

HRID 1367486 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-ff4d2bb326124cd0ad71cd2a15c4d7ba
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Linked notes

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