Triethylamine → 1-(Methylsulfonyl)pyrrolidin-3-yl methanesulfonate

HRID 240602Notes

Reaction equation

HRID 240602 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>ClCCl>[CH3:1][S:2]([O:11][CH:8]1[CH2:9][CH2:10][N:6]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:7]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 982104-Hydroxypyrrolidine

Product 1

HCID 190775631-(Methylsulfonyl)pyrrolidin-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methansulfonyl chloride (1.93 ml) added to an ice cooled solution of 3-pyrrolidinol (871.0 mg) and triethylamine (3.47 ml) in dichloromethane (30.0 ml). After 10 mins the coolant was removed and the mixture was stirred at room temperature for 2 h. The mixture was washed with 10% KHSO4 and 10% aq. K2CO3. The organic layer was passed through a hydrophobic frit and the solvent was evaporated.

Workup

  1. customAfter 10 mins the coolant was removed
  2. washThe mixture was washed with 10% KHSO4 and 10% aq. K2CO3
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c007129c6ab5402782497bd4d69cec56
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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