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

HRID 1727185ノート

反応式

HRID 1727185 の反応式
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

参加物

7

反応物 3

HCID 8471Triethylamine2 回HCID 812191,3-Bis(diphenylphosphino)propaneHCID 866140603-(Cyclopent-3-en-1-ylmethyl)-1,2-dihydropyridin-2-yl trifluoromethanesulfonate

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1afa62e510c64945baf13245d95eb79c
出典データセット
uspto-grants-2009_02
特許番号
US07494992B2

反応ノート

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