N-bromobutanimide → HCID 58598854, compound

HRID 1020326Notes

Reaction equation

HRID 1020326 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CNC(=O)[O-].[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>[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 58598854HCID 58598854, compoundYield 118.1%

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-662437286da94cd88092b7ddb795bb9a
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

Loading…