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

HRID 2056731ノート

反応式

HRID 2056731 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a244e5c7cab34822b5f2eb0206c39364
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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