Thionyl Chloride → (2RS,5SR)-2-Chloromethyl-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([CH2:23]O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>>[Cl:27][CH2:23][CH:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:12]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14]Komponenten
3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A stirred mixture of (2RS,5SR)-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol (1.25 g, 3.58 mmol) and thionyl chloride (2 ml) was heated for 4 h at 80° C. aqueous work-up and crystallization from ethyl acetate/hexane yielded the title compound as an off-white solid (1.12 g, yield 85%), m.p. 130° C. and MS: m/e=367 (M+).