1-Chloroethyl chloroformate → Rel-tert-butyl ((3R,4S)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(methyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([C@@H:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].ClC(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[N:7]([C@@H:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of rac-[(3R,4S)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (3.50 g, 8.04 mmol) in toluene (50 mL) was added under an atmosphere of nitrogen N,N-diisopropyl ethyl amine (1.86 mL, 10.9 mmol). The flask was cooled with a water bath and 1-chloroethyl chloroformate (1.14 mL, 10.5 mmol) was added during 2 min. After stirring for 2 h at ambient temperature the solution stood over night at 5° C. The reaction mixture was concentrated in vacuo. After the addition of methanol (50 mL) it was stirred for 4 h at ambient temperature. Concentration afforded the title compound (2.95 g, 99%) as a light brown oil. MS m/e: 345.1 [M+H]+.
Workup
- temperatureThe flask was cooled with a water bath
- waitstood over night at 5° C
- concentrationThe reaction mixture was concentrated in vacuo
- additionAfter the addition of methanol (50 mL) it
- stirringwas stirred for 4 h at ambient temperature
- concentrationConcentration
Sources & evidence
- ORD record
- ord-653c74167a4e481c97775be2dc14d35c
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226916B2
Reaction notes
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