4-Toluenesulfonyl chloride → [(2R)-5-Oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

HRID 2411351Notes

Reaction equation

HRID 2411351 reaction equation
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>>[O:8]=[C:6]1[NH:7][C@@H:3]([CH2:2][O:1][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 13306710[(2R)-5-Oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonateYield 66.4%

Procedure

Using (R)-5-hydroxymethylpyrrolidin-2-one (1.68 g) and p-toluenesulfonyl chloride (2.92 g) and by the reaction and treatment in the same manner as in Preparation Example 219, the title compound (2.61 g) was obtained.

Workup

  1. customby the reaction and treatment in the same manner
  2. customas in Preparation Example 219

Sources & evidence

ORD record
ord-a7813c03442b436e819f91be025e908a
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…