HCID 68766842, compound → HCID 68769736, compound

HRID 1171599Notes

Reaction equation

HRID 1171599 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([NH:9][C@H](C2C=CC=CC=2)C)[CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:8]1[CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:4][C@H:3]1[CH2:2][OH:1]

Participants

5

Reactant 2

HCID 68766842HCID 68766842, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68769736HCID 68769736, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (3R,4S)-tert-butyl 3-(hydroxymethyl)-4-((S)-1-phenylethylamino)piperidine-1-carboxylate (38 g, 113.6 mMol) and Pd(OH)2 (5 g) were stirred in methanol (250 mL) at rt under 50 psi hydrogen. After overnight stirring, the reaction mixture was filtered through Celite. The solution was concentrated to get the desired product, (3R,4S)-tert-butyl 4-amino-3-(hydroxymethyl)piperidine-1-carboxylate as a pale oil (quantitative yield).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-be9d9deb85f54e69a534c1948920c7f8
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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