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

HRID 1615394Notes

Reaction equation

HRID 1615394 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a9aa21954f4434bba16efad3f4eb22b
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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