HCID 66732679, compound → HCID 66731834, compound

HRID 1963336Notes

Reaction equation

HRID 1963336 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=1)[C:10]([O:12][CH3:13])=[O:11]>CO.[Pt](=O)=O>[ClH:1].[F:21][C:18]1[CH:17]=[C:5]([CH:4]=[C:3]([F:2])[C:19]=1[F:20])[CH2:6][CH:7]1[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][NH:16]1

Participants

4

Reactant 1

HCID 66732679HCID 66732679, compound

Product 1

HCID 66731834HCID 66731834, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 2-(3,4,5-trifluorobenzyl)isonicotinate hydrochloride (4 g, 12.59 mmol) was dissolved in MeOH (45 mL) and platinum(IV) oxide (0.143 g, 0.63 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 3 h. Additional platinum(IV) oxide (0.029 g, 0.13 mmol) was added and the hydrogenation continued for 20 min. The catalyst was filtered off and washed with MeOH. The filtrate was evaporated in vacuo to yield methyl 2-(3,4,5-trifluorobenzyl)piperidine-4-carboxylate hydrochloride (3.96 g, 97%) as a brown solid. MS m/z 288 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. waitthe hydrogenation continued for 20 min
  3. filtrationThe catalyst was filtered off
  4. washwashed with MeOH
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7d24b22d281e4698ada218fb53fc340e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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