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

HRID 908030Notes

Reaction equation

HRID 908030 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-3cef19b5f7434a6c9fdde2290e2b7b53
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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