Methyl 5-(1,8-naphthyridin-2-yl)pentanoate → Methyl 5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanoate

HRID 1004235Notes

Reaction equation

HRID 1004235 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[H][H]>CCO.[Pd].[C]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][NH:11][C:10]=2[N:9]=1

Participants

5

Reactant 2

HCID 11447926Methyl 5-(1,8-naphthyridin-2-yl)pentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11265157Methyl 5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-4 (630 mg, 2.58 mmol) and 10% Pd/carbon (95 mg) in EtOH (25 mL) was stirred under a balloon of hydrogen for 72 h. Following filtration and evaporative removal of the solvent, the residue was chromatographed (silica gel, 70% ethyl acetate/hexanes) to give 1-5 as a colorless oil.

Workup

  1. filtrationfiltration
  2. customremoval of the solvent
  3. customthe residue was chromatographed (silica gel, 70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0bcd7e5842a041228084473322e20461
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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