HCID 117720396, compound → HCID 117720537, compound

HRID 60373Notes

Reaction equation

HRID 60373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH3:24])[CH:15]=2)[C:10]([F:26])([F:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:23][CH3:24])[CH:15]=2)[C:10]([F:26])([F:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 117720396HCID 117720396, compound

Product 1

HCID 117720537HCID 117720537, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-3,3-difluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (230.00 mg) in methanol (10 mL) was added palladium on carbon 10% (10:90, palladium:carbon black, 40 mg). 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 (±)-4-(4-amino-3-methoxy-phenyl)-3,3-difluoro-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 95% yield), which was used without purification. 1H NMR (CDCl3): δ ppm 6.65-6.77 (m, 3H), 4.15-4.65 (m, 2H), 3.85 (s, 3H), 3.77 (br. s., 2H), 2.72-3.13 (m, 3H), 2.03-2.24 (m, 1H), 1.85 (d, J=12.4 Hz, 1H), 1.49 (s, 9H) 3124-67

Workup

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

Sources & evidence

ORD record
ord-32b60429f5c34088b64b1b8d707dacf2
Source dataset
uspto-grants-2016_09
Patent number
US09440984B2

Reaction notes

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