Methoxymethyl-triphenylphosphonium chloride → HCID 18173042, compound

Participants

Reaction Conditions

Reaction Steps

(Methoxymethyl)triphenylphosphonium chloride (296 mg 0.86 mmol) in toluene was cooled in an ice-bath. Potassium bis(trimethylsilyl)amide (2.5 ml, 0.5M in toluene) was added dropwise through a syringe. The mixture was stirred at 0° C. for 1 h. 8-(8-Oxo-bicyclo[3.2.1]oct-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (100 mg) was then added to the mixture, and the mixture was allowed to warm to room temperature and was stirred overnight. Toluene was evaporated off, and the residue was treated with 1N HCl in THF at 70° C. for 3 h. Ethyl acetate was used to extract the product. Column chromatography gave 94 mg of 3-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-8-carbaldehyde as a mixture of cis and trans yield (90%)

Provenance & Evidence