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

HRID 371156Notes

Reaction equation

HRID 371156 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][C@@H: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]>[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][C@@H: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

3

Reactant 1

HCID 70413237N-Ethoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

Product 1

HCID 70412802N-Ethoxycarbonyl-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinolYield 77.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the procedure of Example 4, 423 mg (0.878 mmole) of N-ethoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol and 210 mg of 5% palladium on carbon (50% wet) provides 265 mg (77%) of the title compound as an oil.

Sources & evidence

ORD record
ord-38626a07c57541b898236e2ef736871b
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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