Ethyl (2-Oxo-3-(2-([1,8]naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-acetate → Ethyl (2-Oxo-3-(2-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetate

HRID 322501Notes

Reaction equation

HRID 322501 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>[Pd].CO>[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[N:10]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 1

HCID 53717087Ethyl (2-Oxo-3-(2-([1,8]naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-acetate

Product 1

HCID 54307208Ethyl (2-Oxo-3-(2-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-6 (0.87 g, 2.6 mmol), 10% Pd/C (0.5 g), and CH3OH (25 mL) was stirred under a hydrogen atmosphere (1 atm) for 2 hr. The catalyst was then removed by filtration through a celite pad followed by concentration of the filtrate. Flash chromatogrphy (silica, EtOAc→5% CH3OH/EtOAc) gave 2-7 as a yellow oil.

Workup

  1. customThe catalyst was then removed by filtration through a celite pad

Sources & evidence

ORD record
ord-6c65d1deecb54ce6945ae55e91924fe5
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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