5-Bromoacenaphthene → (3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazine

HRID 2056731노트

반응식

HRID 2056731 반응식
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]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+].Br[C:61]1[C:71]2[C:72]3[C:64]([CH2:65][CH2:66][C:67]=3[CH:68]=[CH:69][CH:70]=2)=[CH:63][CH:62]=1>C1(C)C=CC=CC=1.ClCCl.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]>[CH2:65]1[C:64]2=[C:72]3[C:71](=[CH:61][CH:62]=[CH:63]2)[C:70]([N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[CH:69][CH:68]=[C:67]3[CH2:66]1

참가 물질

8

반응물 4

HCID 749235-BromoacenaphtheneHCID 634876Binap, (A+-)-HCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

생성물 1

HCID 69307361(3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(R)-methylpiperazine (0.124 g, 1.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (49 mg, 0.05 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (69 mg, 0.10 mmol) and sodium tert-butoxide (0.148 g, 1.5 mmol) were stirred in toluene (50 mL) under nitrogen for 15 min to give a blood red solution. 5-Bromo-1,2-dihydroacenaphthylene (0.256 g, 1.1 mmol) was added, the solution stirred under nitrogen and heated at reflux for 3 h. The mixture was cooled, diluted with dichloromethane and filtered through celite. The organic phase was washed with water, dried (MgSO4), filtered and evaporated in vacuo. The crude product was taken forward to the next step without further purification.

후처리

  1. customto give a blood red solution
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through celite
  6. washThe organic phase was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude product was taken forward to the next step without further purification

출처 및 근거

ORD 기록
ord-a244e5c7cab34822b5f2eb0206c39364
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

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