Sodium Bicarbonate → N-Boc-pyrrolidine

HRID 71827

反応式

HRID 71827 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1C1NC(Br)=CN=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 56605248tert-Butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

生成物 1

HCID 643455N-Boc-pyrrolidine収率 76.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

2,6-(bis-pinocolato)diboranonaphthalene (0.501 g), 2-(5-bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.885 g), and NaHCO3 (0.562 g) were dissolved in a mixture of 1,2-dimethoxyethanedichloromethane (15 mL) and water (5 mL). The solution was degassed with nitrogen, and Pd(PPh3)4 (0.0935 g) was added. The reaction mixture was stirred at 90° C. for 16 hours and evaporated under vacuum. Solid was dissolved in DCM (20 mL) and extracted twice with water and once with brine. Solution was evaporated, recrystallized from ethyl acetate, and dried under vacuum, giving 2-(5-{6-[2-(1′-carboxylic acid tert-butyl ester-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.365 g, 46%) as a white solid.

後処理

  1. customThe solution was degassed with nitrogen, and Pd(PPh3)4 (0.0935 g)
  2. additionwas added
  3. customevaporated under vacuum
  4. dissolutionSolid was dissolved in DCM (20 mL)
  5. extractionextracted twice with water and once with brine
  6. customSolution was evaporated
  7. customrecrystallized from ethyl acetate
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-0019f97bbf0843beaec4aa6924336246
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

関連ノート

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