Benzyl Bromide → tert-butyl 5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 2066484ノート

反応式

HRID 2066484 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 11020412tert-butyl 2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

生成物 1

HCID 58117138tert-butyl 5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate収率 59%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (1.0 g, 4.2 mmol) in acetonitrile (20 mL) was added benzyl bromide and the mixture heated at reflux for 2.5 h. The reaction mixture was concentrated in vacuo and the resultant black oil was dissolved in MeOH (50 mL). To this solution was slowly added sodium borohydride (1.2 g, 32.0 mmol) over 10 min, then the mixture was heated at reflux for 2.5 h. After cooling to RT, the reaction mixture was concentrated in vacuo before EtOAc and an aqueous saturated solution of ammonium chloride were added. The reaction mixture was stirred at RT for 1 h. The organic layer was isolated, dried (Na2SO4) and concentrated in vacuo to give the title compound as a cream solid (0.78 g, 59%).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe resultant black oil was dissolved in MeOH (50 mL)
  5. customover 10 min
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 2.5 h
  8. concentrationthe reaction mixture was concentrated in vacuo before EtOAc
  9. additionan aqueous saturated solution of ammonium chloride were added
  10. customThe organic layer was isolated
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2aa68d6b823f4d7b878095600b2357bd
出典データセット
uspto-grants-2012_10
特許番号
US08293735B2

反応ノート

読み込み中…