N-Ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinone → N-Ethoxycarbonyl-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinone

HRID 371153Notes

Reaction equation

HRID 371153 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:7]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=1[O:28]CC1C=CC=CC=1)=[O:5])[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:7]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=1[OH:28])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 13519476N-Ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20274351N-Ethoxycarbonyl-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinoneYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 369 mg (0.77 mmole) of N-ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinone and 414 mg of 5% palladium on carbon (50% wet) in 5 ml ethanol was stirred under 1 atmosphere of hydrogen at 25° C. until the hydrogen uptake is complete (approximately 3 hours). The reaction is filtered through a filter aid, washing with ethanol and the filtrate evaporated in vacuo. The residual crude oil is purified via column chromatography on 22 g of silica gel eluting in 4 ml fractions with 15% ethyl ether in dichloromethane to yield (fractions 28-42) 174 mg (57%) of the title compound as an oil.

Workup

  1. custom(approximately 3 hours)
  2. filtrationThe reaction is filtered through a filter aid
  3. washwashing with ethanol
  4. customthe filtrate evaporated in vacuo
  5. customThe residual crude oil is purified via column chromatography on 22 g of silica gel eluting in 4 ml fractions with 15% ethyl ether in dichloromethane

Sources & evidence

ORD record
ord-6c443097c93248cdbbc61c76e5a4ad1f
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

Loading…