(+/-)-3-Fluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → (+/-)-4-(4-Amino-3-methoxy-phenyl)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester

HRID 60368Notes

Reaction equation

HRID 60368 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)[CH:10]([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)[CH:10]([F:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 117720374(+/-)-3-Fluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 117720142(+/-)-4-(4-Amino-3-methoxy-phenyl)-3-fluoro-piperidine-1-carboxylic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-3-fluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester in methanol (10 mL) was added palladium on carbon 10% (1:9 palladium:carbon black, 40 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (35 PSI) overnight. Filtration through Celite and evaporation of the solvent provided crude (±)-4-(4-amino-3-methoxy-phenyl)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (180 mg, 98%), which was used without purification. 1H NMR (CDCl3): δ ppm 6.63-6.71 (m, 3H), 4.52 (br. s., 2H), 4.05-4.26 (m, 1H), 3.85 (s, 3H), 3.74 (br. s., 2H), 2.63-2.86 (m, 3H), 1.88 (d, J=13.4 Hz, 1H), 1.62-1.79 (m, 1H), 1.49 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-7887f6ba2974422daafd2c8b4de25889
Source dataset
uspto-grants-2016_09
Patent number
US09440984B2

Reaction notes

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