1,3-Dibromopropane → (1-Phenylcyclobutyl)methanamine

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Reaction Steps

(1-Phenylcyclobutyl)methylamine is prepared from phenylacetonitrile (2.93 g, 25 mmol) and 1,3-dibromopropane (7.57 g, 37.5 mmol) as described in Example 1 in 62% yield. The above amine (1.61 g, 10 mmol) is reacted with 6-chloropurine riboside (2.87 g, 10 mmol) as described in Example 1. As the compound did not crystallize it is purified by removal of the solvent under reduced pressure, followed by dissolving the residual gum in ethyl acetate (50 mL) and washing it with water (2×25 mL) and saturated brine (25 mL) and drying (MgSO4). The solvent is removed under reduced pressure and the residual gum is subjected to flash chromatography on silica gel, eluting with 5% CH3OH in CHCl3. N6-((1-phenylcyclobutyl)methyl)adenosine (2.40 g, 58%) is obtained as a white solid foam m.p. 95°-118° C. Found: C, 61.21; H, 6.23; N, 17.24%. C21H25N5O4 calculated requires: C, 61.31; H, 6.08; N, 17.03%.

Provenance & Evidence