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

HRID 1670608Notes

Reaction equation

HRID 1670608 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]([C@@H:10]1[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:9]>N1C=CC=CC=1.ClCCl>[CH3:6][O:7][C:8]([C@@H:10]1[CH2:14][C@@H:13]([O:15][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:9]

Participants

5

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 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (1.56 mol, 179 g) drop wise to a solution of (2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.65 mol, 160 g) in pyridine (600 mL) at 0° C. under a nitrogen atmosphere. Upon complete addition, warm the reaction mixture to room temperature and stir for 2 h. Dilute the reaction mixture with dichloromethane, wash with 0.1 N hydrochloric acid solution and saturated sodium bicarbonate solution. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under vacuum to obtain the title compound (185 g, 91%) as a thick oil. ES-MS m/z 324.1 [M+1]+, 224.0 [M−Boc]+.

Workup

  1. additionUpon complete addition
  2. washwash with 0.1 N hydrochloric acid solution and saturated sodium bicarbonate solution
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-dbacd4ec3db1494eac1422c952007f64
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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