tert-Butyl 3-(1,8-naphthyridin-2-yl)propylcarbamate → 2-(3-(Boc-amino)-propyl)-5,6,7,8-tetrahydro-1,8-naphthyridine

HRID 1004259Notes

Reaction equation

HRID 1004259 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][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[H][H]>CCO.[Pd].[C]>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 11369698tert-Butyl 3-(1,8-naphthyridin-2-yl)propylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 112316322-(3-(Boc-amino)-propyl)-5,6,7,8-tetrahydro-1,8-naphthyridine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 11-6 (4.0 g, 13.9 mmol) and 10% Pd/carbon (4.0 g) in EtOH (100 mL) was stirred under a balloon of hydrogen for 4 h. Following filtration and evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/methanol) to give 11-7 as a white solid.

Workup

  1. filtrationfiltration
  2. customremoval of the solvent
  3. customthe residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-5a45f5d982bf415b9e92aa23b3c5a37b
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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