Methyl 5-methoxypyridine-3-carboxylate → Methyl 5-methoxypiperidine-3-carboxylate

HRID 1465727Notes

Reaction equation

HRID 1465727 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[N:7][CH:8]=1>Cl.CO.[Pt](=O)=O>[CH3:1][O:2][CH:3]1[CH2:8][NH:7][CH2:6][CH:5]([C:9]([O:11][CH3:12])=[O:10])[CH2:4]1

Participants

5

Reactant 1

HCID 16218325Methyl 5-methoxypyridine-3-carboxylate

Product 1

HCID 67033617Methyl 5-methoxypiperidine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 5-methoxypyridine 3-carboxylate (1 g, 6.02 mmol) and platinum (IV) oxide (50 mg) suspended in 1.25 M HCl in methyl alcohol (10 mL) were hydrogenated in Parr shaker under 40 psi overnight. The reaction mixture was filtered through a pad of celite, washed with MeOH and concentrated to give crude product.

Workup

  1. customwere hydrogenated in Parr shaker under 40 psi overnight
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed with MeOH
  4. concentrationconcentrated
  5. customto give crude product

Sources & evidence

ORD record
ord-b08db43995ce49609d6a0676ce25b091
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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