tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 178456946, 화합물

HRID 1620498노트

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HRID 1620498 반응식
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[CH2:16]([NH:19][C:20]1[CH2:24][S:23][C:22](=[O:25])[N:21]=1)[C:17]#[CH:18].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[O:25]=[C:22]1[N:21]=[C:20]([NH:19][CH2:16][C:17]#[CH:18])/[C:24](=[CH:1]/[CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)/[S:23]1

참가 물질

5

반응물 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 3014295Piperidinium acetateHCID 178456890HCID 178456890, 화합물

생성물 1

HCID 178456946HCID 178456946, 화합물수율 76.3%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (11.2 g) in 2-propanol (230 mL) were added 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (16.3 g) and piperidinium acetate (3.90 g). The reaction mixture was stirred at 60° C. overnight, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitate was removed, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (14.0 g).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. customthe precipitate was removed
  4. concentrationthe filtrate was concentrated
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2d1f4c70c0e44e019a253e196f4f8a92
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772277B2

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