Methanesulfonyl chloride → tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 640000

Reaction equation

HRID 640000 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 4183641tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methane sulphonyl chloride (0.39 ml, 5.0 mmol) was added dropwise to a solution of tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (0.51 g, 2.5 mmol) and 4-(dimethylamino)pyridine (0.61 g, 5.0 mmol) in dichloromethane (15 ml). The mixture was stirred at room temperature for 30 minutes and then concentrated to approximately half volume and purified by silica gel chromatography. Elution with a mixture of 3:1 to 1:1 iso-hexane:ethyl acetate yielded tert-butyl 3-{[(methylsulphonyl)oxy]methyl}pyrrolidine-1-carboxylate.

Workup

  1. concentrationconcentrated to approximately half volume
  2. custompurified by silica gel chromatography
  3. washElution
  4. additionwith a mixture of 3:1 to 1:1 iso-hexane

Sources & evidence

ORD record
ord-262b180d5bd640469039c50ef630a6ce
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Linked notes

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