Boron tribromide → 3-Cyclohexyl-1-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one

HRID 1670837Notes

Reaction equation

HRID 1670837 reaction equation
[CH:1]1([CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([O:20]C)=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClC(Cl)C>[CH:1]1([CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 576580123-Cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

Product 1

HCID 576579983-Cyclohexyl-1-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Treat a solution of 3-cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one (1.3 g, 3.66 mmol) in dichloroethane (30 mL) at −20° C. with boron tribromide (1.0 M in DCM, 18.3 mL) for 2 hours. Warm the reaction up to room temperature and stir for 12 hours. Quench the reaction with methanol and remove the solvent under vacuum. Partition the residue with ethyl acetate and HCl (1 N). Wash the organic with water. After drying the organic layer, filtrate and concentrate to afford 1.2 g (99%) of the title compound. MS (m/z): 342 (M+).

Workup

  1. temperatureWarm
  2. customthe reaction up to room temperature
  3. customQuench
  4. customthe reaction with methanol
  5. customremove the solvent under vacuum
  6. customPartition the residue with ethyl acetate and HCl (1 N)
  7. washWash the organic with water
  8. customAfter drying the organic layer, filtrate
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-c559225c42224dd398c353ab9f7ab4c9
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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