Propionyl chloride → 1-[5-(4-Bromo-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propan-1-one

HRID 1482941Notes

Reaction equation

HRID 1482941 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([N:11]2[CH2:12][CH:13]3[CH2:14][N:15]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:16][CH:17]3[CH2:18]2)=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 90079376(4-Bromo-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone hydrochloride

Product 1

HCID 900793731-[5-(4-Bromo-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propan-1-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.3 (4-Bromo-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone hydrochloride (300 mg; 0.9 mmol) is dissolved in 5 ml of DCM, N-ethyldiiso-propylamine for synthesis (0.46 ml; 2.7 mmol) is added and then cooled to 0° C. Propionyl chloride for synthesis (0.095 ml; 1.09 mmol) is added dropwise followed by stirring at RT for 14 h. The reaction mixture is separated between DCM and water. The organic layer is separated, dried over MgSO4, filtered off and then reduced to dryness under vacuo to afford 316 mg (99.5%) 1-[5-(4-bromo-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propan-1-one 3 as a brown oil.

Workup

  1. additionis added
  2. additionis added dropwise
  3. customThe reaction mixture is separated between DCM and water
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-bde100fca3e44a6aba2578924ac99ee6
Source dataset
uspto-grants-2016_08
Patent number
US09416133B2

Reaction notes

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