Triethylamine → Methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate

HRID 9942Notes

Reaction equation

HRID 9942 reaction equation
C(N(CC)CC)C.Cl.[OH:9][C@H:10]1[CH2:14][N:13]([CH3:15])[C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1.[S:20](Cl)([CH3:23])(=[O:22])=[O:21].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:23][S:20]([O:9][C@H:10]1[CH2:14][N:13]([CH3:15])[C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1)(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86590358Methyl (2S,4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylate hydrochloride

Product 1

HCID 12082503Methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Triethylamine (1.53 mL) was added to a suspension of methyl (2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylate hydrochloride (1 g) obtained from Reference example 1 or 3 in tetrahydrofuran (10 mL) and the mixture was stirred at 40° C. for 3 hours. Mesyl chloride was added to the mixture under ice cooling and the mixture was stirred for 2 hours. Ethyl acetate (20 mL) and 5% aqueous sodium hydrogencarbonate solution (10 mL) were added to the reaction mixture, which was then extracted. The organic layer was separated from the aqueous layer and the solvent of the organic layer was removed by distillation under reduced pressure to give the title compound (1.0 g, yield 83%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionwas then extracted
  3. customThe organic layer was separated from the aqueous layer
  4. customthe solvent of the organic layer was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1588a0231fd14c6f8e892efabb879249
Source dataset
uspto-grants-2006_08
Patent number
US07091363B2

Reaction notes

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