Carbon tetrabromide → tert-Butyl 3-(2,2-dibromovinyl)piperidine-1-carboxylate

HRID 1172730Notes

Reaction equation

HRID 1172730 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][CH:34]([CH:38]=O)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][CH:34]([CH:38]=[C:1]([Br:5])[Br:2])[CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 99644481-Boc-piperidine-3-carboxaldehyde

Product 1

HCID 86615128tert-Butyl 3-(2,2-dibromovinyl)piperidine-1-carboxylateYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of CBr4 (1.63 g, 4.92 mmol) and PPh3 (1.29 g, 4.92 mmol 9 in DCM (25 ml) was added 1 g (4.69 mmol) 3-Formyl-piperidine-1-carboxylic acid tert-butyl ester (commercially available) at room temperature. The reaction mixture was stirred at R.T for 24 h and the solvent was removed. The crude product was purified by flash chromatography (cyclohexane/AcOEt 90/10) to afford 0.15 g (9%) of 3-(2,2-Dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. customthe solvent was removed
  2. customThe crude product was purified by flash chromatography (cyclohexane/AcOEt 90/10)

Sources & evidence

ORD record
ord-27be1bbcc21b45d59f66f1d3dff0c65a
Source dataset
uspto-grants-2010_11
Patent number
US07834035B2

Reaction notes

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