Methyl 5-(3-(trifluoromethyl)phenyl)nicotinate → HCID 66660068, compound

HRID 383793Notes

Reaction equation

HRID 383793 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:7][CH:8]=1>CO>[F:19][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:10][NH:11][CH2:12][C@@H:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:18]2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 20099856Methyl 5-(3-(trifluoromethyl)phenyl)nicotinate

Product 1

HCID 66660068HCID 66660068, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-[3-(trifluoromethyl)phenyl]nicotinate (190.1 mg) in MeOH (30 ml) was hydrogenated (ca. 4 atm) for 2 days in a Parr low-pressure hydrogenation apparatus with a 5 wt. % Rh on Al2O3 catalyst (121.6 mg) at 90° C. Rh on Al2O3 catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified with silica gel column chromatography (eluent: CHCl3/MeOH=98/2˜90/10) to give methyl cis-5-[3-(trifluoromethyl)phenyl]piperidine-3-carboxylate (71.2 mg) as a pale brown oil.

Workup

  1. customfor 2 days
  2. customat 90° C
  3. filtrationRh on Al2O3 catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified with silica gel column chromatography (eluent: CHCl3/MeOH=98/2˜90/10)

Sources & evidence

ORD record
ord-95f59ce656494788a705b66b1be1ea88
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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