trans-1-Benzyl-4-(4-methoxyphenyl)piperidin-3-ol → (+/-) trans-4-(4-Methoxyphenyl)-piperidin-3-ol

HRID 1507182Notes

Reaction equation

HRID 1507182 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([OH:22])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C@@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]2[OH:22])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 118207341trans-1-Benzyl-4-(4-methoxyphenyl)piperidin-3-ol

Product 1

HCID 96770188(+/-) trans-4-(4-Methoxyphenyl)-piperidin-3-olYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of trans-1-benzyl-4-(4-methoxyphenyl)piperidin-3-ol (9 g, 30 mmol) in methanol (150 mL) was added 10% Pd/C (4.8 g) and the reaction was stirred overnight under a hydrogen atmosphere. The catalyst was then removed by filtration through Celite and the solvent was evaporated under reduced pressure to give (+/−) trans-4-(4-methoxyphenyl)-piperidin-3-ol (5.1 g, 24.6 mmol, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.10-7.15 (m, 2H) 6.80-6.86 (m, 2H) 4.30 (d, J=5.27 Hz, 1H) 3.37-3.43 (m, 1H) 3.04 (dd, J=11.58, 4.36 Hz, 1H) 2.86 (d, J=12.17 Hz, 1H) 2.43 (td, J=12.09, 2.67 Hz, 1H) 2.22-2.35 (m, 2H) 1.57-1.63 (m, 1H) 1.43-1.54 (m, 1H).

Workup

  1. customThe catalyst was then removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-47aecff38e88469fb3b14ee0e05c48e4
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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