Kfm 19 → 1,3-Dipropyl-8-(1-hydroxycyclopent-3-yl)xanthine

HRID 1682110Notes

Reaction equation

HRID 1682110 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH:15]3[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]3)=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH3:23])[C:5]1=[O:6])[CH2:2][CH3:3]>C(O)C>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]3)=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH3:23])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 131584Kfm 19

Product 1

HCID 103813391,3-Dipropyl-8-(1-hydroxycyclopent-3-yl)xanthineYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g (1.6 mmol) of 1,3-dipropyl-8-(1-oxo-3-cyclopentyl)xanthine, 10 ml of ethanol and 0.1 g (2.6 mmol) of sodium tetrahydridoboranate are stirred for 21/2 days at ambient temperature. The mixture is evaporated down in vacuo and mixed with water and methylene chloride then the aqueous phase is acidified and extracted. The combined organic extracts are dried and evaporated down in vacuo. The residue is separated into the isomers by chromatography on silica gel (CH2Cl2 /C3OH 95:5). From the 1st fraction, 0.4 g of the title compound are obtained in the form of white crystals (39% of theory), m.p. 174°-176° C. and from the 2nd fraction 0.4 g of the title compound are obtained in the form of white crystals (39% of theory), m.p. 191°-193° C.

Workup

  1. customThe mixture is evaporated down in vacuo
  2. additionmixed with water and methylene chloride
  3. extractionextracted
  4. customThe combined organic extracts are dried
  5. customevaporated down in vacuo
  6. customThe residue is separated into the isomers by chromatography on silica gel (CH2Cl2 /C3OH 95:5)

Sources & evidence

ORD record
ord-158c7fe588a84453854ff3e192b81623
Source dataset
uspto-grants-1992_12
Patent number
US05175291

Reaction notes

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