反应详情

1-Chloroethyl chloroformate (1.5 mL, 13.9 mmol) was added to a solution of (3S,4R)-methyl 1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate (4.20 g, 11.5 mmol) in DCE (50 mL) at 0° C. The mixture was refluxed for 1 hour. After cooling, the solvent was removed under vacuum at 65° C. for 1 hour. MeOH (50 mL) was added to the residue and refluxed for 1 hour. The MeOH was removed. The solid was re-dissolved in CHCl3 and treated with saturated Na2CO3. The aqueous portion was separated and extracted with CHCl3 (2×30 mL). The organic phase was combined and dried. The solvent was removed to afford (3S,4R)-methyl 4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate (3.1 g, 98%). (LCMS (APCI+) [M+H]+274.1; Rt: 2.25 min.).

1. temperatureThe mixture was refluxed for 1 hour
2. temperatureAfter cooling
3. customthe solvent was removed under vacuum at 65° C. for 1 hour
4. additionMeOH (50 mL) was added to the residue
5. temperaturerefluxed for 1 hour
6. customThe MeOH was removed
7. dissolutionThe solid was re-dissolved in CHCl3
8. additiontreated with saturated Na2CO3
9. customThe aqueous portion was separated
10. extractionextracted with CHCl3 (2×30 mL)
11. customdried
12. customThe solvent was removed