5-(1,1-dimethylheptyl)-2-[3-hydroxy-5-(N-methoxycarbonylamino)pentyl]phenol → N-Methoxycarbonyl-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinol

HRID 371162Notes

Reaction equation

HRID 371162 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[CH:12][C:13]([CH2:17][CH2:18][CH:19]([OH:27])[CH2:20][CH2:21][NH:22][C:23]([O:25][CH3:26])=[O:24])=[C:14]([OH:16])[CH:15]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>[Pd]>[CH3:26][O:25][C:23]([N:22]1[CH2:21][CH2:20][C@H:19]([OH:27])[CH2:18][C@@H:17]1[C:13]1[CH:12]=[CH:11][C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][C:14]=1[O:16][CH2:2][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:24].[CH3:26][O:25][C:23]([N:22]1[CH2:21][CH2:20][C@H:19]([OH:27])[CH2:18][C@@H:17]1[C:13]1[CH:12]=[CH:11][C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][C:14]=1[OH:16])=[O:24]

Participants

4

Reactant 1

HCID 202743645-(1,1-dimethylheptyl)-2-[3-hydroxy-5-(N-methoxycarbonylamino)pentyl]phenol

Product 2

HCID 70413105N-Methoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinolHCID 70414022N-Methoxycarbonyl-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinolYield 57%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Debenzylation of 177 mg (0.377 mmole) of N-methoxycarbonyl cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol with 144 mg of 5% palladium on carbon (50% wet) by the procedure of Example 4 affords 81.3 mg (57%) of the title compound as an oil, 4.1 mg (3%) of by-product 5-(1,1-dimethylheptyl)-2-[3-hydroxy-5-(N-methoxycarbonylamino)pentyl]phenol as an oil, and 49.2 mg (35%) of a mixture of the two.

Sources & evidence

ORD record
ord-03f1175bf5314a3882bbcc303c6bea9b
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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