Methyl 2-(3-tert-butylphenyl)isonicotinate hydrochloride → Methyl 2-(3-tert-butylphenyl)piperidine-4-carboxylate

HRID 1963150Notes

Reaction equation

HRID 1963150 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][CH:11]=1)([CH3:5])([CH3:4])[CH3:3]>CO.[Pt](=O)=O>[C:2]([C:6]1[CH:7]=[C:8]([CH:12]2[CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][CH2:20][NH:21]2)[CH:9]=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66731606Methyl 2-(3-tert-butylphenyl)isonicotinate hydrochloride

Product 1

HCID 66731564Methyl 2-(3-tert-butylphenyl)piperidine-4-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 2-(3-tert-butylphenyl)isonicotinate hydrochloride (3 g, 9.81 mmol) was dissolved in methanol (100 mL) and platinum(IV) oxide (0.111 g, 0.49 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 13 h. To the mixture was added platinum(IV) oxide (40 mg), and the mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and satd NaHCO3 were added and the phases separated. Washed with brine, passed through a phase separator and evaporated to yield methyl 2-(3-tert-butylphenyl)piperidine-4-carboxylate (2.56 g, 95%) as a brown oil.

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. customwas hydrogenated in a Büchi hydrogenator at room temperature
  3. wait5 bar for 1 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with MeOH
  6. additionwere added
  7. customthe phases separated
  8. washWashed with brine
  9. customevaporated

Sources & evidence

ORD record
ord-d9e70a7b14da4395a9a78fc4f95b2a0d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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