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

HRID 1467769Notes

Reaction equation

HRID 1467769 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-8ebc94792d4a4ec787e13f0b841bf6a0
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

Loading…