Ethyl 4-(1,8-naphthyridin-2-yl)butanoate → Ethyl 4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butanoate

HRID 618165Notes

Reaction equation

HRID 618165 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[H][H]>CCOC(C)=O.[Pd]>[NH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:1]=2)[CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 10955797Ethyl 4-(1,8-naphthyridin-2-yl)butanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22594332Ethyl 4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 19-3 (2.3 g, 9.4 mmol) in 50 mL EtOAc was treated with 10% Pd/C (230 mg) and a hydrogen balloon. After 4 d the reaction filtered through celite, concentrated, and purified by flash chromatography (silica, 70% EtOAc/hexane), providing 19-4 as a yellow oil.

Workup

  1. filtrationAfter 4 d the reaction filtered through celite,
  2. concentrationconcentrated
  3. custompurified by flash chromatography (silica, 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-0243bed824ca40b9818bd7d2a12f067d
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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