Cyclopropanecarboxaldehyde → N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{2-[(cyclopropylmethyl)amino]ethyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

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Reaction Steps

The title compound was prepared by a similar method to example 5 from N-{2-(2-aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (430 mg, 0.58 mmol) (preparation 18), cyclopropanecarbaldehyde (45 mg, 0.64 mmol) and sodium triacetoxyborohydride (270 mg, 1.27 mmol) in tetrahydrofuran (10 ml). The product was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane rising in polarity to dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (360 mg) as a gum. MS: 788 (MH+).

Provenance & Evidence