3-(6,7,8,9-Tetrahydro-benzo[b]-[1,8]naphthyridin-8-yl)-propionic acid ethyl ester → 3-(1,2,3,4,6,7,8,9-Octahydro-benzo[b]-[1,8]naphthyridin-8-yl)-propionic acid ethyl ester

HRID 379246Notes

Reaction equation

HRID 379246 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:20][C:11]2=[N:12][C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:19]=[C:10]2[CH2:9][CH2:8]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:20][C:11]2=[N:12][C:13]3[NH:14][CH2:15][CH2:16][CH2:17][C:18]=3[CH:19]=[C:10]2[CH2:9][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 538305493-(6,7,8,9-Tetrahydro-benzo[b]-[1,8]naphthyridin-8-yl)-propionic acid ethyl ester

Product 1

HCID 544215783-(1,2,3,4,6,7,8,9-Octahydro-benzo[b]-[1,8]naphthyridin-8-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 14-2 (0.298 g, 1.05 mmol) and Pd on carbon (0.060 g) in ethanol (10 mL) was placed under 1 atm of H2 and stirred for 12 h. The solution was concentrated. The residue was purified by flash chromatography (5% MeOH in CH2Cl2) to give 14-3.

Workup

  1. concentrationThe solution was concentrated
  2. customThe residue was purified by flash chromatography (5% MeOH in CH2Cl2)
  3. customto give 14-3

Sources & evidence

ORD record
ord-fe1d7c8845e64c9da89095b918127897
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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