HCID 66711203, compound → Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate

HRID 2200121Notes

Reaction equation

HRID 2200121 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]=2)=[C:6]([C:23]([F:26])([F:25])[F:24])[CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[C:6]([C:23]([F:26])([F:24])[F:25])[CH:5]=1

Participants

4

Reactant 1

HCID 66711203HCID 66711203, compound

Product 1

HCID 90028532Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir the mixture of tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (289 mg, 0.776 mmol), methanol (50 mL) and Pd/C (10%, 25 mg) under hydrogen atmosphere for 30 hrs. Remove H2, filter the mixture and concentrate the filtrate under reduced pressure. Purify the residue with flash chromatography (silica gel, PE:EtOAc=5:1) to afford the desired product (151 mg, 84%).

Workup

  1. filtrationRemove H2, filter the mixture
  2. concentrationconcentrate the filtrate under reduced pressure
  3. customPurify the residue with flash chromatography (silica gel, PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-5e7f0689e76a4efa9024bce6a5b89c36
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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