Acetic Acid → 2-(3,4-dichlorophenyl)-1-{(4aRS,8SR,8aRS)-4-[(1H-imidazol-5-yl)methyl]-8-(pyrrolidin-1-yl)perhydroquinoxalin-1-yl}ethan-1-one

HRID 1876818ノート

反応式

HRID 1876818 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:27]1[C:31]([CH:32]=O)=[CH:30][N:29]=[CH:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:15]([CH2:32][C:31]3[NH:27][CH:28]=[N:29][CH:30]=3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 764281H-Imidazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

生成物 1

HCID 687783942-(3,4-dichlorophenyl)-1-{(4aRS,8SR,8aRS)-4-[(1H-imidazol-5-yl)methyl]-8-(pyrrolidin-1-yl)perhydroquinoxalin-1-yl}ethan-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (134 mg, 0.34 mmol) was dissolved in absolute CH2Cl2 (10 ml), and 1H-imidazole-5-carbaldehyde (65 mg, 0.67 mmol), NaBH(OAc)3 (143 mg, 0.67 mmol) and glacial acetic acid (41 mg, 0.67 mmol) were added. The mixture was stirred at room temperature for 2.5 hours. The mixture was then filtered and the organic phase was extracted by shaking three times with HCl (1 N). The aqueous phase was brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was purified by preparative HPLC (as described under Example 14 in MeOH/H2O/Et2NH 80:20:0.1). MeOH was evaporated off from the product fraction, the aqueous phase was extracted by shaking three times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated. A colorless solid was isolated.

後処理

  1. filtrationThe mixture was then filtered
  2. extractionthe organic phase was extracted
  3. stirringby shaking three times with HCl (1 N)
  4. extractionextracted
  5. stirringby shaking three times with CH2Cl2
  6. dry with materialThe organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residue was purified by preparative HPLC (as described under Example 14 in MeOH/H2O/Et2NH 80:20:0.1)
  9. customMeOH was evaporated off from the product fraction
  10. extractionthe aqueous phase was extracted
  11. stirringby shaking three times with CH2Cl2
  12. dry with materialthe combined organic phases were dried over Na2SO4
  13. customevaporated
  14. customA colorless solid was isolated

出典と根拠

ORDレコード
ord-997bd85458ec4458a743184be9b84684
出典データセット
uspto-grants-2012_11
特許番号
US08309725B2

反応ノート

読み込み中…