Tetrabutylammonium Fluoride → HCID 9851658, compound

Participants

Reaction Steps

N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{2-[(cyclohexylmethyl)amino]ethyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (210 mg, 0.25 mmol) (preparation 23) was dissolved in stirred tetrahydrofuran (1 ml) and a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 ml, 1 mmol) added. The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure and the residue partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate. The organic layer was separated and the aqueous phase extracted with ethyl acetate. The ethyl acetate phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:6:0.6) increasing in polarity to (91:9:0.9). This gave the title compound (70 mg) as a powder. MS: 601 (MH+).

Provenance & Evidence