반응 #169554

반응 방정식

1-Chloroethyl chloroformate

(3S,4R)-methyl 1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

→

(3S,4R)-methyl 4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

수율 98.3%

용매

DCE

반응 조건

후처리

1. 1
   온도The mixture was refluxed for 1 hour
2. 2
   온도After cooling
3. 3
   기타the solvent was removed under vacuum at 65° C. for 1 hour
4. 4
   workup.ADDITIONMeOH (50 mL) was added to the residue
5. 5
   온도refluxed for 1 hour
6. 6
   기타The MeOH was removed
7. 7
   workup.DISSOLUTIONThe solid was re-dissolved in CHCl3
8. 8
   workup.ADDITIONtreated with saturated Na2CO3
9. 9
   기타The aqueous portion was separated
10. 10
    추출extracted with CHCl3 (2×30 mL)
11. 11
    기타dried
12. 12
    기타The solvent was removed

실험 절차

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.).

출처