1-(Pyridin-4-yl)piperidine-4-carboxylic acid → (1-(Pyridin-4-YL)piperidin-4-YL)methanol

HRID 412512노트

반응식

HRID 412512 반응식
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.B.O1CCCC1>O1CCCC1>[OH:14][CH2:13][CH:10]1[CH2:9][CH2:8][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:12][CH2:11]1

참가 물질

4

반응물 2

HCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under an argon atmosphere, to a solution of 1-(pyridin-4-yl)piperidine-4-carboxylic acid (Tetrahedron, vol. 44, No. 23, page 7095 (1988)) (500 mg) in tetrahydrofuran (5 ml) was added 1M borane-tetrahydrofuran solution (14.5 ml) with ice-cooling, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in 12% hydrochloric acid and stirred at 50° C. for 1 hour. The reaction mixture was neutralized with aqueous sodium hydrogencarbonate and 4N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and dried under reduced pressure to give the title compound (400 mg).

후처리

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionthe obtained residue was dissolved in 12% hydrochloric acid
  8. stirringstirred at 50° C. for 1 hour
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-2323eb6dea95474aa3ed3d573ce4b9e2
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562828B1

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