Reaction #1784878

Reaction equation

(2S,4R)-4-acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

dichloromethane

potassium carbonate

→

crude title compound

Yield 88.0%

(2S,4R)-4-Mercapto-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Yield 88.0%

Solvents

MeOH

Conditions

Workup

1. 1
   OtherAfter the starting material was consumed the solvent
2. 2
   Otherwas evaporated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in water
4. 4
   Extractionextracted with EtOAc (2×200 ml)
5. 5
   WashThe combined organic layers were washed with brine
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Otherevaporated

Procedure

To a solution of (2S,4R)-4-acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (12.5 g, 41 mmol; CAS Reg. No. 188111-18-4) in MeOH (200 ml) and dichloromethane (20 ml) was added potassium carbonate (5.7 g, 41.2 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 1 h. After the starting material was consumed the solvent was evaporated. The residue was dissolved in water and extracted with EtOAc (2×200 ml). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated to get the crude title compound (9.5 g, 36.1 mmol; 88%) which was used in next step without further purification. MS (ESI): m/z=262.0 [M+H]+.

Source