Water → HCID 22941881, compound

HRID 361540Notes

Reaction equation

[CH3:1][C@H:2]([CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8].C[N+]1([O-])CCOCC1.[OH2:33].S([O-])([O-])=O.[Na+].[Na+].CC(C)=O.[OH2:44]>>[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]([OH:44])[C:22]([OH:33])([CH3:23])[CH3:24])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8]

Participants

Reactant 5

HCID 962Water

HCID 24437Sodium Sulfite

HCID 82029Methyl morpholine oxide

HCID 18366337Propan-2-one--water (1/1)

HCID 22861486HCID 22861486, compound

Product 1

HCID 22941881HCID 22941881, compoundYield 97%

Procedure

A solution of 1-(4-(R)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine (0.48 g, 1.44 mmol), 4-methylmorpholine-N-oxide (0.51 g, 4.38 mmol) and potassium osmate dihydrate (5 mg, 0.015 mmol) in acetone/water 1:2 (9 mL) was stirred for 16 hours. Water (10 mL) and sodium sulfite (1 g) were added and the reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×30 ml) using dried magnesium sulfate and the solvent evaporated to yield 0.51 g (97% yield) 1-(4-(R)-Methyl-7,8-dihydroxy-8-methylnonyl)-3,7-dimethylxanthine (inventive compound no. 2537R) as a colorless oil.

Workup

extractionThe reaction mixture was extracted with dichloromethane (3×30 ml)
customthe solvent evaporated

Sources & evidence

ORD record: ord-d2bfd436031f47edadc403a3e1d350d1
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866576

Reaction notes

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