4,4'-Dibromobiphenyl → Ethyl (3ar,6ar)-1-(4'-bromo-1,1'-biphenyl-4-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1h)-carboxylate

HRID 1947389

반응식

HRID 1947389 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:21]1[CH2:25][CH2:24][C@@H:23]2[CH2:26][N:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][C@H:22]12>ClCCl>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:21]3[CH2:25][CH2:24][C@@H:23]4[CH2:26][N:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][C@H:22]34)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 71104,4'-DibromobiphenylHCID 10796Cesium carbonateHCID 24743918(3AR,6AR)-5-Ethoxycarbonyl-1H-hexahydropyrrolo[3,4-B]pyrrole

생성물 1

HCID 67397057Ethyl (3ar,6ar)-1-(4'-bromo-1,1'-biphenyl-4-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1h)-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

The catalyst solution was added to the vessel containing the 4,4′-dibromobiphenyl, cesium carbonate, and the product of Example 41C and the mixture was heated to 98° C. for 12 hours. The mixture was cooled to 20° C. and 80 g of dichloromethane was added. The resulting mixture was stirred and then filtered to remove the catalyst. The resulting solution was concentrated under reduced pressure and the residue was purified by column chromatography to yield 5.65 g of the title compound.

후처리

  1. additionThe catalyst solution was added to the vessel
  2. filtrationfiltered
  3. customto remove the catalyst
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-5e9959faad2b4997bcd71b1aa74fc6e8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399468B2

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