(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl 8-(N-(trifluoroacetoxy)aminomethyl)xanthine → (R)-1-(5-acetoxyhexyl)-3-methyl-8-(N-(trifluoroacetoxy)aminomethyl)xanthine

HRID 1296408Notes

Reaction equation

HRID 1296408 reaction equation
[C:1]([O:4][C@H:5]([CH3:38])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17](CC3C=CC=CC=3)[C:16]([CH2:28][NH:29][O:30][C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[N:15][C:14]=2[N:13]([CH3:37])[C:11]1=[O:12])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:38])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([CH2:28][NH:29][O:30][C:31](=[O:36])[C:32]([F:35])([F:33])[F:34])=[N:15][C:14]=2[N:13]([CH3:37])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86585572(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl 8-(N-(trifluoroacetoxy)aminomethyl)xanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 86585573(R)-1-(5-acetoxyhexyl)-3-methyl-8-(N-(trifluoroacetoxy)aminomethyl)xanthineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl-8-(N-(trifluoroacetoxy)aminomethyl)xanthine (1.0 g, 1.9 mmol) and 10% palladium on carbon (50% water, 300 mg) in glacial acetic acid (50 ml) was treated with hydrogen gas (80 psi) on a Parr sharker at room temperature for 18 hours. After filtering through a pad of celite, the filtrate was concentrated under reduced pressure to provide (R)-1-(5-acetoxyhexyl)-3-methyl-8-(N-(trifluoroacetoxy)aminomethyl)xanthine (700 mg, 85% yield) as a white powder.

Workup

  1. filtrationAfter filtering through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c56b87e4057d4fa1937843a9fe3d9ffd
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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