Hydrochloric Acid → (S)-1-(5-hydroxyhexyl)-7-benzyl-3-methylxanthine

HRID 1814976Notes

Reaction equation

HRID 1814976 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C@@H:22]([O:24]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH3:23])[C:13](=[O:36])[N:12]([CH3:37])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C@@H:22]([OH:24])[CH3:23])[C:13](=[O:36])[N:12]([CH3:37])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53988311(S)-7-benzyl-1-(5-(4-nitrobenzoyloxy)hexyl)-3-methylxanthine

Product 1

HCID 11610099(S)-1-(5-hydroxyhexyl)-7-benzyl-3-methylxanthineYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-7-benzyl-1(5-(4-nitrobenzoyloxy)hexyl)-3-methylxanthine (25 g, 49.5 mmol) was added to a solution for sodium hydroxide (3.36 g, 84 mmol) in methanol (200 ml). After stirring for 2 hours, the pH was adjusted to 4 by addition of 1 N hydrochloric acid solution. After concentrating under reduced pressure, the residue was partitioned between water (150 ml) and ethyl acetate (300 ml). The organic layer was washed with saturated aqueous sodium chloride solution (150 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% hexane-ethyl acetate to provide (S)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine (14 g). c) A mixture of (S)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine (14 g, 39 mmol), acetic acid (100 ml), methanol (50 ml), and 10% palladium on carbon (5 g) was treated with hydrogen gels (40 psi) for 14 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate to give (S)-1-(5-hydroxyhexyl)-3-methylxanthine (6.5 g).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was partitioned between water (150 ml) and ethyl acetate (300 ml)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution (150 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20% hexane-ethyl acetate

Sources & evidence

ORD record
ord-a7c066fb3ce74f8aba5aa66b6c24f37a
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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