HCID 66711841, compound → HCID 66711166, compound

HRID 1262131Notes

Reaction equation

HRID 1262131 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@:11]([OH:25])([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH3:24])[CH:15]=2)[C@@H:10]([OH:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:23][CH3:24])[CH:15]=2)([OH:25])[C@@H:10]([OH:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66711841HCID 66711841, compound

Product 1

HCID 66711166HCID 66711166, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (±)-(3S,4S)-3,4-dihydroxy-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylicacid tert-butyl ester (540 mg) in ethanol (30 mL) was added palladium on carbon 10% (78.00 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (˜max 25-30 PSI) for 5 h. Filtration through Celite and evaporation of the solvent provided (±)-(3S,4S)-4-(4-amino-3-methoxy-phenyl)-3,4-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester in quantitative yield.

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent

Sources & evidence

ORD record
ord-b5d16bc1a3d24f5cbebe4d06530d11b2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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