Reaction #10039

Reaction equation

Potassium thioacetate

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

Ethyl acetate

sodium chloride

→

title compound

Yield 97.4%

Methyl (2S, 4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate

Yield 97.4%

Solvents

ethanol water

Conditions

Workup

1. 1
   workup.WAITto stand overnight at the same temperature
2. 2
   Extractionwas then extracted
3. 3
   OtherThe organic layer was separated from the aqueous layer, which
4. 4
   Washwas washed with water (10 mL)
5. 5
   OtherThe solvent of the organic layer was removed by distillation under reduced pressure

Procedure

Potassium thioacetate (677 mg) was added to a solution of methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate (609 mg) obtained from Reference example 4 in ethanol/water (9:1) (6 ml), and the resulting mixture was stirred at 80° C. for 3 hours, and then the mixture was allowed to stand overnight at the same temperature. Ethyl acetate (20 mL) and 10% aqueous sodium chloride solution (10 mL) were added to the reaction mixture, which was then extracted. The organic layer was separated from the aqueous layer, which was washed with water (10 mL). The solvent of the organic layer was removed by distillation under reduced pressure to give the title compound (543 mg, yield 97%).

Source