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

HRID 1482941
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HRID 1482941 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bde100fca3e44a6aba2578924ac99ee6
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09416133B2

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