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Benzophenone imine → 2-(Benzhydrylideneamino)-7-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-fluoren-9-one

HRID 553059
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HRID 553059 반응식
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([N:15]4[CH2:22][CH:21]5[CH:17]([CH2:18][N:19]([CH3:23])[CH2:20]5)[CH2:16]4)=[CH:9][CH:10]=3)[C:5](=[O:24])[C:4]=2[CH:3]=1.[C:25](=[NH:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:25](=[N:38][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([N:15]4[CH2:22][CH:21]5[CH:17]([CH2:18][N:19]([CH3:23])[CH2:20]5)[CH2:16]4)=[CH:9][CH:10]=3)[C:5](=[O:24])[C:4]=2[CH:3]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
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참가 물질

7

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 671645522-Bromo-7-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-fluoren-9-one

생성물 1

HCID 866211422-(Benzhydrylideneamino)-7-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-fluoren-9-one수율 100%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
90 °C

실험 절차

A mixture of the product of Example 61A (332 mg, 0.867 mmol), benzophenone imine (180 μL, 1.07 mmol; Aldrich), tris(dibenzylideneacetone)dipalladium (0) (Pd2 dba3; 32 mg, 0.035 mmol; Alfa), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 54 mg, 0.087 mmol; Strem) and sodium tert-butoxide (125 mg, 1.30 mmol; Aldrich) in 5 mL toluene was flushed with nitrogen and heated at 90° C. for 18 h. The reaction mixture was cooled to ambient temperature and filtered through diatomaceous earth, rinsing with EtOAc. After concentrating the solution under reduced pressure, the residue was purified by column chromatography (90 g silica gel, 1-12% gradient of NH4OH-MeOH (1:10) in CH2Cl2) to afford the title compound, which was slightly impure (489 mg, >100% yield): MS (DCI/NH3): m/z 484 (M+1)+.

후처리

  1. customwas flushed with nitrogen
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationfiltered through diatomaceous earth
  4. washrinsing with EtOAc
  5. concentrationAfter concentrating the solution under reduced pressure
  6. customthe residue was purified by column chromatography (90 g silica gel, 1-12% gradient of NH4OH-MeOH (1:10) in CH2Cl2)

출처 및 근거

ORD 기록
ord-6ee5658e142f4d8d91128ffab70dc3a0
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951791B2

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