Benzyl chloroformate → Benzyl 2-(4-bromo-3-fluorophenyl)pyrrolidine-1-carboxylate

HRID 415153Notes

Reaction equation

HRID 415153 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][C:3]=1[F:13].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>O1CCOCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:4][C:3]=1[F:13]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 534036242-(4-Bromo-3-fluorophenyl)pyrrolidine

Product 1

HCID 66620873Benzyl 2-(4-bromo-3-fluorophenyl)pyrrolidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-Bromo-3-fluorophenyl)pyrrolidine (12.5 g, 51.4 mmol) was dissolved in a mixture of dioxane (180 mL) and water (120 mL) and treated with potassium carbonate (28.4 g, 0.21 mol) and benzyl chloroformate (9.65 g, 56.5 mmol) at ambient temperature overnight. The mixture was partitioned between ethyl acetate and brine. The organic phase was concentrated and the residue was purified by flash chromatography on silica gel using a gradient of 5-20% ethyl acetate in petroleum ether to give benzyl 2-(4-bromo-3-fluorophenyl)pyrrolidine-1-carboxylate as a yellow solid (15.3 g, yield 82%). LC-MS (ESI) m/z: 378 (M+1)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. concentrationThe organic phase was concentrated
  3. customthe residue was purified by flash chromatography on silica gel using a gradient of 5-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-db67a18a4bc049eeaf20bf5f28878f7e
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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