Triethylamine → 6,9-Dihydro-5H-6,9-methanocyclohepta[b]pyridine

HRID 1727185노트

반응식

HRID 1727185 반응식
FC(F)(F)S(O[CH:7]1[C:12]([CH2:13][CH:14]2[CH2:18][CH:17]=[CH:16][CH2:15]2)=[CH:11][CH:10]=[CH:9][NH:8]1)(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:17]12[CH2:18][CH:14]([CH:15]=[CH:16]1)[CH2:13][C:12]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 8471Triethylamine2회HCID 812191,3-Bis(diphenylphosphino)propaneHCID 866140603-(Cyclopent-3-en-1-ylmethyl)-1,2-dihydropyridin-2-yl trifluoromethanesulfonate

생성물 1

HCID 688081066,9-Dihydro-5H-6,9-methanocyclohepta[b]pyridine수율 77%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3-(cyclopent-3-en-1-ylmethyl)-1,2-dihydropyridin-2-yl trifluoromethanesulfonate (Preparation 26, 3.1 g, 10.1 mmol) in dimethylformamide (20 ml) stirred under nitrogen was added 1,3-bis(diphenylphosphino)propane (0.334 g, 0.8 mmol), triethylamine (1.52 g, 16.6 mmol) and palladium (II) acetate (0.072 g, 0.32 mmol). The reaction mixture was warmed to 100° C. and stirred for 18 h. Triethylamine (1 ml) was added and the reaction mixture was warmed to 110° C. for a further 6 h. The reaction mixture was cooled and poured into saturated brine solution (50%, 75 ml), and the product was extracted with ethyl acetate (4×30 ml). The combined organic extracts were washed with water (2 times), sodium hydrogen carbonate solution and brine before drying (Na2SO4) and concentrating in vacuo. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (15:85) to give a colourless oil (1.07 g, 77%).

후처리

  1. temperaturethe reaction mixture was warmed to 110° C. for a further 6 h
  2. temperatureThe reaction mixture was cooled
  3. extractionthe product was extracted with ethyl acetate (4×30 ml)
  4. washThe combined organic extracts were washed with water (2 times), sodium hydrogen carbonate solution and brine
  5. dry with materialbefore drying (Na2SO4)
  6. concentrationconcentrating in vacuo
  7. customThe crude oil was purified by flash chromatography
  8. washeluting with ethyl acetate:hexane (15:85)

출처 및 근거

ORD 기록
ord-1afa62e510c64945baf13245d95eb79c
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07494992B2

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