Methanesulfonyl chloride → 1-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 1361283Notes

Reaction equation

HRID 1361283 reaction equation
[C:1]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[C:1]([N:8]1[CH2:12][C@H:11]([O:13][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2S,4R)-1-Bochydroxypyrrolidine-2-carboxylate (8 g, 32.65 mmol) prepared in Step B in DCM was added dropwise TEA (11.99 ml, 81.56 mmol) and methanesulfonyl chloride (3.77 ml, 48.9 mmol) at m° C. After the reaction mixture was stirred at rt for 3 h, the organic extracts were washed with a saturated NaHCO3 aqueous solution, 1N HCl and brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (9.4 g, 90%).

Workup

  1. washthe organic extracts were washed with a saturated NaHCO3 aqueous solution, 1N HCl and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e8380938cfc449d8da92831f7dc2df8
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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