Triethylamine → 1-(4-Chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-methylsulphonyloxymethylcyclopentane

HRID 847445Notes

Reaction equation

HRID 847445 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:23]=[CH:22][C:10]([CH2:11][CH:12]2[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[C:13]2([OH:21])[CH2:19][OH:20])=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH:12]2[CH2:16][CH2:15][C:14]([CH3:17])([CH3:18])[C:13]2([OH:21])[CH2:19][O:20][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 147219041-(4-Chlorobenzyl)-2-hydroxy-2-hydroxymethyl-3,3-dimethylcyclopentane

Product 1

HCID 147219061-(4-Chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-methylsulphonyloxymethylcyclopentaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.76 g (1.05 equivalents)methylsulphonyl chloride were added to a solution of 6.42 g (24 mmols) 1-(4-chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-hydroxymethylcyclopentane prepared as described in (i) and 2.55 g (1.1 equivalents) triethylamine in 50 ml dichloromethane at 10°-15° C. The reaction mixture was kept at 10°-15° C. for further 2 hours and then washed with 20 ml water, then 20 ml aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulphate and flashed. Trituration with 60/80 petroleum gave 6.64 g 1-(4-chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-methylsulphonyloxymethylcyclopentane (Isomer A) as a white solid, m.pt. 113°-114° C. Yield: 80%.

Workup

  1. customprepared
  2. washwashed with 20 ml water
  3. dry with material20 ml aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-591a6be051ce443e9cfff5e6d9818dc7
Source dataset
uspto-grants-1992_08
Patent number
US05142061

Reaction notes

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