Methanol → 4-(4-Benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde

HRID 1615394노트

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HRID 1615394 반응식
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.CO.[Cl-].[Na+]>ClCCl>[CH2:21]([O:20][C:18]([NH:17][CH:14]1[CH2:13][CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=2)[CH2:16][CH2:15]1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 21273587HCID 21273587, 화합물HCID 66691942Ethyl 4-(4-(benzyloxycarbonylamino)piperidin-1-yl)benzoate

생성물 1

HCID 866745294-(4-Benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

The 4-(4-benzyloxycarbonylaminopiperidin-1-yl)-benzoic acid ethyl ester (13.6 g, 35.6 mmol) obtained in Example 7 (2) was dissolved in dichloromethane (150 ml), and a diisobutylaluminum hydride-hexane solution (91 ml, 89.0 mmol) was added thereto, followed by stirring at −78° C. for 1 hour. Methanol was added to the reaction mixture, and then saturated sodium chloride was added thereto, followed by stirring. After the insoluble material was filtered with Celite, the solvent was evaporated from the filtrate under reduced pressure. The obtained residue was dissolved in dichloroethane (180 ml), and manganese dioxide (38.0 g) was added thereto, followed by stirring at 60° C. for 21 hours. After the insoluble material was filtered with Celite, the solvent was evaporated from the filtrate under reduced pressure, thereby obtaining 4-(4-benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde (7.0 g, 58%) as a white solid.

후처리

  1. stirringby stirring
  2. filtrationAfter the insoluble material was filtered with Celite
  3. customthe solvent was evaporated from the filtrate under reduced pressure
  4. dissolutionThe obtained residue was dissolved in dichloroethane (180 ml)
  5. additionmanganese dioxide (38.0 g) was added
  6. stirringby stirring at 60° C. for 21 hours
  7. filtrationAfter the insoluble material was filtered with Celite
  8. customthe solvent was evaporated from the filtrate under reduced pressure

출처 및 근거

ORD 기록
ord-9a9aa21954f4434bba16efad3f4eb22b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765750B2

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