Sodium triacetoxyborohydride → HCID 9917154, compound

Participants

Reaction Steps

A solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (323 mg, 0.66 mmol), 2-(methoxymethyl)benzaldehyde (109 mg, 0.73 mmol) (Tetrahedron 4739, 47, 1991) and 1 drop of acetic acid in tetrahydrofuran (15 ml) was stirred at room temperature for 24 hr. Sodium triacetoxyborohydride (310 mg, 1.45 mmol) was then added and the reaction mixture stirred for 1 hr. At this point the solvent was partially removed under reduced pressure and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The solvent was removed from the organic layer under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3) increasing in polarity to dichloromethane:methanol:ammonia (95:5:0.5). This gave the title compound (250 mg) as a foam. MS: 625 (MH+).

Provenance & Evidence