4-Toluenesulfonyl chloride → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyloxymethyl)-cyclopentanecarboxylic acid ethyl ester

HRID 1367542Notes

Reaction equation

HRID 1367542 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[CH2:19][OH:20])=[O:5])[CH3:2].C(N(CC)CC)C.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14])[CH2:8][C@H:7]1[CH2:19][O:20][S:34]([C:31]1[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=1)(=[O:36])=[O:35])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59619451(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 86649030(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyloxymethyl)-cyclopentanecarboxylic acid ethyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (example 68 step 4, 500 mg) and triethyl amine (836 mg) in dichloromethane (5 mL) was added toluene-4-sulfonyl chloride (1.53 g). The reaction mixture was stirred overnight at room temperature then partitioned between hydrochloric acid (1N) and dichloromethane. The aqueous layers was extracted with dichloromethane and the combined organic layers were washed with half saturated aqueous solution of sodium hydrogenocarbonate and brine, then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethyl acetate (1:0 to 19:1 v/v) as eluant to afford the title compound (602 mg, 80%) as a yellow liquid.

Workup

  1. customthen partitioned between hydrochloric acid (1N) and dichloromethane
  2. extractionThe aqueous layers was extracted with dichloromethane
  3. washthe combined organic layers were washed with half saturated aqueous solution of sodium hydrogenocarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethyl acetate (1:0 to 19:1 v/v) as eluant

Sources & evidence

ORD record
ord-f0d689fa1a2f48348a8724704a74ff96
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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