Ammonium formate → 4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine

HRID 380533Notes

Reaction equation

HRID 380533 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([O:23][C:24](=[O:33])[C@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CO>[C:17]1([CH2:16][CH:15]([O:23][C:24](=[O:33])[C@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 599707671-Benzyl-4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine

Product 1

HCID 599707654-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.310 g (0.7 mmol) of 1-benzyl-4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidine (Step 1a, isomer 1a), 0.8 g of ammonium formate, and 0.3 g of Pearlman's Catalyst (Pd(OH)2, 20% Pd, moist, Degussa type) in 20 mL of methanol was heated at reflux for 1 h. The mixture was cooled to rt and filtered through a pad of celite and concentrated to afford isomer 1b of the title compound which was used without further purification.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7f13b656011640bb9238b44c6a5c82cd
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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