HCID 20773493, compound → HCID 20773495, compound

HRID 1814965Notes

Reaction equation

HRID 1814965 reaction equation
[OH:1][C@@H:2]([CH3:35])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14](CC3C=CC=CC=3)[C:13]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:12][C:11]=2[N:10]([CH3:34])[C:8]1=[O:9].[H][H]>C(O)C.[Pd]>[OH:1][C@@H:2]([CH3:35])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[N:12][C:11]=2[N:10]([CH3:34])[C:8]1=[O:9]

Participants

5

Reactant 2

HCID 20773493HCID 20773493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20773495HCID 20773495, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-1-(5-hydroxyhexyl)-7-benzyl-8-(N-BOC-aminomethyl)-3-methylxanthine (0.6 g, 1.24 mmol) in ethanol (60 ml) was added 10% palladium on carbon catalyst (0.5 g). The mixture was treated with hydrogen gas (50 psi) on a Parr shaker for 18 hours. Removal of the catalyst by filtration and evaporation of the solvent under reduced pressure provides (S)-1-(5-hydroxyhexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.4 g, 82% yield) as a white solid.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-784dbaf8b87345bcb245fd414f0f3a0b
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

Loading…