Benzyl chloroformate → Phenylmethyl 2-(4-bromophenyl)-1-pyrrolidinecarboxylate

HRID 1968148Notes

Reaction equation

HRID 1968148 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 42814942-(4-Bromophenyl)pyrrolidine

Product 1

HCID 59222259Phenylmethyl 2-(4-bromophenyl)-1-pyrrolidinecarboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-bromophenyl)pyrrolidine (2.26 g, 10 mmol) in dioxane (18 mL) and water (12 mL) was added potassium carbonate (5.52 g, 40 mol) and benzyl chloroformate (1.88 g, 11 mmol) at ambient temperature and stirred overnight. Then the mixture was partitioned between ethyl acetate and brine. The organic phase was concentrated in vacuo and the residue was purified by column chromatography (silica gel, EtOAc:hexane=1:10) to give the title compound (2.95 g, 82%) as a colorless oil. LC-MS (ESI) m/z: 360 (M+1)+.

Workup

  1. customThen the mixture was partitioned between ethyl acetate and brine
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe residue was purified by column chromatography (silica gel, EtOAc:hexane=1:10)

Sources & evidence

ORD record
ord-5d19ff338a6944b7ac6acfaa604712a9
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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