N-bromobutanimide → HCID 86602860, compound

HRID 508519Notes

Reaction equation

HRID 508519 reaction equation
[CH2:1]1[C:6](=O)[N:5]([Br:8])[C:3](=[O:4])C1.CNC(=O)[O-:12].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1>CC#N.O.CCOC(C)=O>[CH2:6]([NH:5][C:3](=[O:12])[O-:4])[CH3:1].[CH3:14][O:15][C:16]1[C:17]([Br:8])=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 86602861HCID 86602861, compound

Product 1

HCID 86602860HCID 86602860, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

NBS (70 mg, 0.4 mmol) was added to a solution of N-methylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, step A) (0.1 g, 0.36 mmol) in CH3CN (3.6 mL), and stirred overnight at room temperature. The reaction was diluted with H2O and EtOAc and filtered through an Extrelut column. The column was washed with EtOAc and the filtrate was concentrated to afford 120 mg (94%) of the subtitle compound. MS calculated for C16H20BrNO3+H: 342, observed: 342.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-74e9279a805e43aba091e3557ca5b909
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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