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

Temperature

2.5 °C

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).

1. customAfter completion of the reaction
2. customthe water in the reaction mixture was removed by distillation under reduced pressure
3. additionAcetic acid (10 mL) and ethyl acetate (20 mL) were added to the residue, which
4. customThe crystals which precipitated
5. filtrationwere collected by filtration

ORD record

ord-c90dc2dd01f949469059e8711881967f

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091363B2