Dimethylformamide → HCID 131727762, compound

HRID 1435941Notes

Reaction equation

HRID 1435941 reaction equation
[CH3:1][C:2]1[C:11]2[NH:10][C:9](=O)[C@@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[Br:28]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[Br:28][C:4]1[CH:3]=[C:2]([CH3:1])[C:11]2[NH:10][CH2:9][C@@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:7]3[C:6]=2[CH:5]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 131727758HCID 131727758, compound

Product 1

HCID 131727762HCID 131727762, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of (±)-cis tert-butyl 6-methyl-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate from Example 19, Part A (0.87 g, 3.0 mmol) in 15 mL of THF and 4 mL of DMF at −30° C. was added N-bromosuccinimide (0.56 g, 3.15 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 0.99 g (90%) 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-9f3e2b3441e3439db40fc9461c92b87b
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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