N-bromobutanimide → N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 546304Notes

Reaction equation

HRID 546304 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([NH:11][C:12](=[O:14])[O-:13])[CH3:10].[CH3:15][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>C(#N)C.C(Cl)Cl.O>[CH2:9]([NH:11][C:12](=[O:13])[O-:14])[CH3:10].[CH3:15][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 86602856HCID 86602856, compound

Product 1

HCID 86602858N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

NBS (34 mg, 0.2 mmol) was added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 21, Step A) (50 mg, 0.2 mmol) in acetonitrile (1 mL), and stirred overnight at room temperature. The reaction was diluted with CH2Cl2 (3 mL) and H2O (3 mL) and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-50% EtOAc-hexanes gradient to afford the subtitle compound. MS calculated for C16H20BrNO2+H: 338, observed: 338.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-16b510aa0d424ffaaa223d6d33c29be9
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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