Hydrochloric Acid → (R)-1-(5-hydroxyhexyl)-7-methylxanthine

HRID 1814978Notes

Reaction equation

HRID 1814978 reaction equation
[OH-].[K+].C([O:6][C@H:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[NH:15][C:13]1=[O:14])(=O)C.Cl>CO.O>[OH:6][C@H:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[NH:15][C:13]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 53687917(R)-1-(5-acetoxyhexyl)-7-methylxanthine

Product 1

HCID 53844332(R)-1-(5-hydroxyhexyl)-7-methylxanthineYield 76.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Potassium hydroxide (1.0 g, 17.8 mmol) was added to a solution of (R)-1-(5-acetoxyhexyl)-7-methylxanthine (prepared as described for CT12460) (3.8 g, 12.3 mmol) in methanol-water (1:1, 100 ml). After stirring for 3 hours, the pH of the solution was adjusted to 7 by the slow addition of 1 N hydrochloric acid. The solution was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with 15% methanol-ethyl acetate to provide (R)-1-(5-hydroxyhexyl)-7-methylxanthine (2.5 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel eluting with 15% methanol-ethyl acetate

Sources & evidence

ORD record
ord-db34d0eb6a8a481f80909dadbd7fdffa
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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