Hydrochloric Acid → (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester

HRID 1367489Notes

Reaction equation

HRID 1367489 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([OH:11])[CH2:8][C@H:7]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:8][C@H:7]1[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66919043(1R,2R)-2-(4-Chloro-phenoxymethyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 86649021(1R,2R)-2-(4-Chloro-phenoxymethyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (ice bath) solution of (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 312 mg) and triethylamine (528 mg) in dichloromethane (6 mL) was added methanesulfonyl chloride (580 mg). The reaction mixture was stirred 36 h at room temperature then hydrochloric acid (1N) was added. The reaction mixture was extracted with dichloromethane. The combined organic layers were washed with an aqueous half-saturated solution of sodium carbonate and half saturated brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (3:1 to 3:1 v/v) as eluant to afford the title compound (0.380 g, 97%) as a light yellow oil. MS (EI): 377.1 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane
  2. washThe combined organic layers were washed with an aqueous half-saturated solution of sodium carbonate and half saturated brine
  3. dry with materialthen dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (3:1 to 3:1 v/v) as eluant

Sources & evidence

ORD record
ord-f834a807321b4934b379e35dc9b4b22a
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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