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

HRID 842310Notes

Reaction equation

HRID 842310 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([O:17][C:18]([N:20]1[CH2:24][C@H:23]([OH:25])[CH2:22][C@H:21]1[C:26]([O:28][CH3:29])=[O:27])=[O:19])([CH3:16])([CH3:15])[CH3:14].O>O1CCCC1>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@H:23]([O:25][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:22][C@H:21]1[C:26]([O:28][CH3:29])=[O:27])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 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-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (14.8 ml, 106.0 mM) and methanesulfonyl chloride (6.9 ml, 90.0 mM) were added to a solution of methyl (2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (20 g, 81.5 mM) in anhydrous tetrahydrofuran (200 ml) under ice-cooling in a nitrogen gas stream, and the mixture was stirred for 30 minutes. The reaction mixture was poured into water followed by extracting with ethyl acetate, the organic layer was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate and the solvent was removed to give the title compound almost quantitatively (27 g).

Workup

  1. temperaturecooling in a nitrogen gas stream
  2. extractionby extracting with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous solution of ammonium chloride
  4. dry with materiala saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-840c0223f9b946aebc97294333fee475
Source dataset
uspto-grants-2002_04
Patent number
US06372914B1

Reaction notes

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