Benzyl Bromide → 2,5-Dibenzyl-4,6-dioxooctahydropyrrolo[3,4-c]pyridine

HRID 1892Notes

Reaction equation

HRID 1892 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([N:14]1[CH2:22][CH:21]2[CH:16]([C:17](=[O:24])[NH:18][C:19](=[O:23])[CH2:20]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:7]([N:14]1[CH2:22][CH:21]2[CH:16]([C:17](=[O:24])[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19](=[O:23])[CH2:20]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 196912212-Benzyl-4,6-dioxooctahydropyrrolo[3.4-c]pyridine

Product 1

HCID 196913492,5-Dibenzyl-4,6-dioxooctahydropyrrolo[3,4-c]pyridineYield 111.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 905 mg of K2CO3 and 400 mg of the compound from step 457b in 5 mL of DMF was added 308 mg of benzyl bromide, and the reaction mixture was stirred at room temperature under N2 for 6.5 hours. The mixture was diluted with ethyl acetate, which was washed with water and brine, dried and concentrated to give 610 mg of the title compound.

Workup

  1. washwas washed with water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eb07eb00507a464db46f471df4d8364d
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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