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

HRID 5081Notes

Reaction equation

HRID 5081 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]([O:17][C:18]([N:20]1[CH2:28][CH:27]([OH:29])[CH2:26][C@H:21]1[C:22]([O:24][CH3:25])=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[Na+]>O1CCCC1>[C:13]([O:17][C:18]([N:20]1[CH2:28][C@H:27]([O:29][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:26][C@H:21]1[C:22]([O:24][CH3:25])=[O:23])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 121855781-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.02 ml of methanesulfonyl chloride, followed by 3.65 ml of triethylamine were added, whilst ice-cooling, to a solution of 6.1 g of methyl 1-(t-butoxycarbonyl)-4-hydroxyprolinate [prepared as described in step (6) above] dissolved in 120 ml of dry tetrahydrofuran. The mixture was stirred first at 0° to 5° C. for 1 hour and then at room temperature for 1 hour, after which it was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 8.13 g of the title compound as an oil.

Workup

  1. additionwere added, whilst ice-
  2. waitat room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-372a5e01fff64e0fb51a06075258f893
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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