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

HRID 371155Notes

Reaction equation

HRID 371155 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][C@@H:3]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][C:10]=1[O:24]CC1C=CC=CC=1>[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][C@@H:3]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][C:10]=1[OH:24]

Participants

3

Reactant 1

HCID 70491050N-Methyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

Product 1

HCID 70492367N-Methyl-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinolYield 84.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the procedure of Example 4, 1.13 g (2.68 mmole) of N-methyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol and 452 mg of 5% palladium on carbon (50% wet) affords 0.752 g (84%) of the title compound as an oil.

Sources & evidence

ORD record
ord-c3c01f44d5d544d2bbbedbd3850d9d48
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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