Triethylamine → Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCN(CC)CC.[S:25](Cl)([CH3:28])(=[O:27])=[O:26]>ClCCl>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][O:15][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1Participants
5
Procedure
To a stirred of 1-(4-trifluoromethyl-phenyl)-cyclopentyl]-methanol (239) (15 g, 61.47 mmol) in dichloromethane (200 mL) was added Et3N (17.1 mL, 123 mmol) followed by mesyl chloride (5.7 mL, 73.77 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h. After completion, the reaction was quenched by the addition of water. The reaction mixture was diluted with dichloromethane. The organic part was washed with water, separated, dried over Na2SO4 and finally concentrated. The crude product was purified by 100-200 silica column chromatography using 10% ethyl acetate in hexane as the eluent to give methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester (240) (14 g, 70.6%) as a white solid.
Workup
- customAfter completion, the reaction was quenched by the addition of water
- additionThe reaction mixture was diluted with dichloromethane
- washThe organic part was washed with water
- customseparated
- dry with materialdried over Na2SO4
- concentrationfinally concentrated
- customThe crude product was purified by 100-200 silica column chromatography
Sources & evidence
- ORD record
- ord-114586647b7d4f008c393d4051bc9cd1
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045486B2
Reaction notes
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