Tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-phenylbenzoate → Tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-phenylbenzoate

HRID 454596Notes

Reaction equation

HRID 454596 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12]

Participants

5

Reactant 1

HCID 66990319Tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 58508450Tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-phenylbenzoateYield 74.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-phenylbenzoate (0.13 g) in ethyl acetate (1 mL) and methanol (1 mL), 10% palladium-carbon (63 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Ethyl acetate was added to the reaction mixture, and the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration to obtain 0.081 g of tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-phenylbenzoate as a yellow solid.

Workup

  1. additionwas added
  2. customthe insoluble substance was removed by filtration
  3. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  4. additionwas added to the obtained residue
  5. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-38b42412375949588ea94ecc679df9ce
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…