HCID 118483556, compound → HCID 118483465, compound

HRID 58417Notes

Reaction equation

HRID 58417 reaction equation
[F:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[C:4]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1>CCO.[Pd]>[F:1][C:2]1[C:3]([C:21]([F:24])([F:22])[F:23])=[C:4]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 118483556HCID 118483556, compound

Product 1

HCID 118483465HCID 118483465, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-(3-fluoro-2-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (3, 4.7 g, 13.6 mmol) and 10% Pd/C (1.0 g) in EtOH (100 mL) was placed under an atmosphere of H2 (30 psi) at ambient temperature for 18 h. the mixture was filtered through a Celite, and the filtrate was concentrated under reduced pressure to give tert-butyl 4-(3-fluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate (4) as a clear oil (4.80 g, >99%): 1H NMR (300 MHz, DMSO-d6) δ 7.72-7.60 (m, 1H), 7.46 (d, J=8.1 Hz, 1H), 7.30 (dd, J=12.3, 8.1 Hz, 1H), 4.18-4.00 (m, 2H), 3.11-2.95 (m, 1H), 2.92-2.64 (m, 2H), 1.76-1.51 (m, 4H), 1.42 (s, 9H).

Workup

  1. filtrationthe mixture was filtered through a Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9bd00fd2ac79422c8a3682739d645ba0
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

Loading…