(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine → (R)-1-(5-acetoxyhexyl)-3-methylxanthine

HRID 1296412Notes

Reaction equation

HRID 1296412 reaction equation
[C:1]([O:4][C@H:5]([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17](CC3C=CC=CC=3)[CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 53701360(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 69155058(R)-1-(5-acetoxyhexyl)-3-methylxanthineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (13.0 g, 32.6 mmol) and 10% palladium on carbon (50% water, 3.6 g) in glacial acetic acid (160 ml) was treated with hydrogen gas (50 psi) on a Parr shaker for 16 hours. After filtering through a pad of celite, the filtrate was concentrated under reduced pressure to provide (R)-1-(5-acetoxyhexyl)-3-methylxanthine (9.6 g, 96% yield) as a white colored solid.

Workup

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

Sources & evidence

ORD record
ord-78217cf84e27401bb12e2c402f155022
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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