N-bromobutanimide → HCID 59494587, compound

HRID 872020Notes

Reaction equation

HRID 872020 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1>C(#N)C>[Br:1][C:26]1[CH:25]=[C:24]([O:27][CH3:28])[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:22][C:21]=1[CH2:20][N:12]([CH:9]1[CH2:11][CH2:10]1)[C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67545206HCID 67545206, compound

Product 1

HCID 59494587HCID 59494587, compoundYield 137.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (978 mg) was added to a solution of tert-butyl cyclopropyl[4-methoxy-3-(3-methoxypropoxy)benzyl]carbamate (6.36 g) in acetonitrile (50 ml) under ice cooling and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo and the resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate/=4/1 to 3/1) to give tert-butyl [2-bromo-4-methoxy-5-(3-methoxypropoxy)benzyl]cyclopropylcarbamate (3.35 g) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate/=4/1 to 3/1)

Sources & evidence

ORD record
ord-2edf361b8b994e5bb6f837a1756048ca
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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