Acetic Acid → 2-(s)-Dibenzylamino-3-phenyl-1-piperidin-2-(r/s)-yl-propan-1-(r)-ol

HRID 1436484Notes

Reaction equation

HRID 1436484 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>[Pt].CO>[CH2:25]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C@@H:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)[OH:11])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 690163992-(S)-Dibenzylamino-3-phenyl-1-pyridin-2-yl-propan-1-(S)-olHCID 178418361HCID 178418361, compound

Product 1

HCID 1317277752-(s)-Dibenzylamino-3-phenyl-1-piperidin-2-(r/s)-yl-propan-1-(r)-olYield 94.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Add 2-(S)-dibenzylamino-3-phenyl-1-pyridin-2-yl-propan-1-(S)-ol (1.05 g, 2.57 mmol), 5% platinum on carbon sulfided (215 mg), glacial acetic acid (2 mL) and methanol (40 mL) and stir 18 h under 1 atmosphere of hydrogen gas. Add filter agent, filter and concentrate. Add ethyl acetate and wash with saturated aqueous sodium bicarbonate, dry (magnesium sulfate) and concentrate to give the title compound as a white foam (1.005 g, 94%).

Workup

  1. additionAdd
  2. filtrationfilter agent
  3. filtrationfilter
  4. concentrationconcentrate
  5. washAdd ethyl acetate and wash with saturated aqueous sodium bicarbonate
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-2afb7c27e723409cbb29360627a17091
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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