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

HRID 1507242Notes

Reaction equation

HRID 1507242 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 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-rel-(3S,4S)-1-benzyl-4-(4-methoxyphenyl)piperidin-3-ol (7 g, 23.5 mmol) in methanol (100 mL) was added 10% Pd/C (3.76 g) and the reaction mixture was stirred overnight under a hydrogen atmosphere (balloon pressure). The catalyst was removed by filtrathou through Celite and the solvent was evaporated under reduced pressure to give (±)-rel-(3S,4S)-4-(4-methoxyphenyl)piperidin-3-ol (4.8 g, 89% yield). LCMS (method F) RT 1.485 (61.5% AP) m/z 207.8 (M+H+), 1.536 (29.7% AP), m/z 207.8 (M+H+); 1H NMR (DMSO-d6) δ 7.133 (d, J=7, 2H), 6.83 (d, J=7, 2H), 4.31 (br s, 1H), 3.7 (s, 3H), 3.02 (m, 1H), 2.86 (d, J=12, 1H), 2.45 (m, 1H), 2.22-2.39 (m, 2H), 1.62-1.61 (m, 1H), 1.610-1.46 (m, 1H).

Workup

  1. customThe catalyst was removed
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6631999de730414b98ecd2b896f94741
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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