Triethylamine → 1-(Methylsulfonyl)pyrrolidin-3-yl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][S:2]([N:6]1[CH2:10][CH2:9][CH:8]([O:11][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:7]1)(=[O:4])=[O:3]Participants
6
Procedure
Methanesulphonyl chloride (1.95 ml, 25.3 mmol) was added dropwise to an ice-cooled, stirred solution of 3(R,S)-pyrrolidinol (1.0 g, 11.5 mmol), triethylamine (3.5 ml, 25.3 mmol) and 4-dimethylaminopyridine (70 mg, 0.575 mmol) in dichloromethane (10 ml) under nitrogen. The resulting slurry was stirred at room temperature for 24 hours, then diluted with dichloromethane (50 ml), washed successively with saturated aqueous sodium bicarbonate solution (50 ml) and water 50 ml), dried (Na2SO4) and filtered. Dilution of the filtrate with ethyl acetate provided the title compound (1.67 g) as a white crystalline solid. Rf 0.84 (SS 1). Found: C,29.89; H,5.12; N,5.74. C6H13NO5S2 requires C,29.62; H,5.39; N,5.76%.
Workup
- temperaturecooled
- washwashed successively with saturated aqueous sodium bicarbonate solution (50 ml) and water 50 ml),
- dry with materialdried (Na2SO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2dea765dc09b411ab1c2d7026312ec18
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05770611
Reaction notes
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