Veratraldehyde → HCID 9917413, compound

Participants

Reaction Steps

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (200 mg, 0.4 mmol) was dissolved in stirred tetrahydrofuran (5 ml) and 3,4-dimethoxybenzaldehyde (130 mg, 0.8 mmol) added. The reagents were stirred together until everything had dissolved and then sodium triacetoxyborohydride (130 mg, 0.6 mmol) added. The reaction mixture was stirred for 24 hr and then quenched by the addition of methanol (1 ml). 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 (95:5:0.5) increasing to (92:7:1). This gave the title compound (90 mg) as a foam. MS: 641 (MH+).

Provenance & Evidence