HCID 86661683, compound → HCID 66712084, compound

HRID 1262133Notes

Reaction equation

HRID 1262133 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[CH:16]=3)[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C@@H:12]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH3:25])[CH:16]=2)[C@@H:10]([OH:11])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86661683HCID 86661683, compound

Product 1

HCID 66712084HCID 66712084, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(3-methoxy-4-nitro-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (190 mg, 0.542 mmol) in methanol (10.00 mL) was added palladium on carbon 10% (40.00 mg), and the mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (35 PSI) for 2 h. Filtration through Celite and evaporation of the solvent provided crude (±)-(3R,4S)-4-(4-amino-3-methoxy-phenyl)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (173 mg, 99%), which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-c84af4d684e34e958d6cc8e4e0d7aae2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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