Dimethylformamide → HCID 68971616, compound

HRID 1435931Notes

Reaction equation

HRID 1435931 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=O)[C@@H:9]3[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1.CN(C=O)C.[Br:29]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[Br:29][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[NH:11][CH2:10][C@@H:9]3[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@@H:8]3[C:7]=2[CH:6]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 131727755HCID 131727755, compound

Product 1

HCID 68971616HCID 68971616, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of (±)-cis tert-butyl 6-methoxy-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate from Example 10, Part B (0.39 g, 1.28 mmol) in 8 mL of THF and 4 mL of DMF at −30° C. was added N-bromosuccinimide (0.15 g, 1.34 mmol). The reaction was stirred at −30° C. for 1 h and then was diluted with water and ethyl acetate. The organics were washed with water and brine, dried (Na2SO4) and concentrated in vacuo to afford 0.41 g (83%) of the title compound which was used without purification.

Workup

  1. washThe organics were washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30bf1d1f7e73477ba32a7129e75b21d2
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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