Reaction #10040

Reaction equation

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

hydrochloric acid

→

title compound

Yield 95.0%

(2S, 4S)-4-mercapto-1-methyl-2-pyrrolidinecarboxylic acid hydrochloride

Yield 95.0%

Solvents

water

Conditions

Workup

1. 1
   OtherAfter completion of the reaction
2. 2
   Otherthe water in the reaction mixture was removed by distillation under reduced pressure
3. 3
   workup.ADDITIONAcetic acid (10 mL) and ethyl acetate (20 mL) were added to the residue, which
4. 4
   OtherThe crystals which precipitated
5. 5
   Filtrationwere collected by filtration

Procedure

A mixed solution of methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate (10.7 g), concentrated hydrochloric acid (14.9 g) and water (16 mL) was stirred at from 75 to 85° C. for 5 hours. After completion of the reaction, the water in the reaction mixture was removed by distillation under reduced pressure. Acetic acid (10 mL) and ethyl acetate (20 mL) were added to the residue, which was stirred at from 0 to 5° C. for 1 hour. The crystals which precipitated were collected by filtration to give the title compound (9.2 g, yield 95%). Nuclear magnetic resonance spectrum (400 MHz, CDCl3) δ(ppm): 2.11–2.20 (m, 1H), 2.97–3.05 (m, 1H), 3.02 (s, 3H), 3.56–3.68 (m, 2H), 3.80–3.88 (m, 1H), 4.35–4.41 (m, 1H).

Source