Sodium Bicarbonate → N-Boc-pyrrolidine

HRID 71827

반응식

HRID 71827 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 643455N-Boc-pyrrolidine수율 76.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0019f97bbf0843beaec4aa6924336246
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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