1-Chloroethyl chloroformate → methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride
Reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C@@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC(Cl)=O>C(#N)C>[ClH:19].[Cl:20][C:15]1[CH:14]=[C:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1[Cl:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the compound (33.4 g) obtained in step 2 in acetonitrile (250 mL) was added ACE-Cl (13.9 g) at room temperature, and the mixture was stirred at 90° C. for 2 hr. The reaction solution was cooled, and the solvent was evaporated under reduced pressure. To the residue was added methanol (250 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction solution was cooled, the solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/IPE to give methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride (26.9 g, 98%) as a pale-yellow powder.
Workup
- temperatureThe reaction solution was cooled
- customthe solvent was evaporated under reduced pressure
- additionTo the residue was added methanol (250 mL)
- stirringthe mixture was stirred at 80° C. for 2 hr
- temperatureThe reaction solution was cooled
- customthe solvent was evaporated under reduced pressure
- washthe residue was washed with ethyl acetate/IPE
Sources & evidence
- ORD record
- ord-07ae5e7febea407397f4f809797c8df5
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592454B2
Reaction notes
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