Sodium Hydroxide → [(1S,4R)-4-(2-amino-6-butoxy-purin-9-yl)cyclopent-2-en-1-yl]methanol

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Reaction Steps

A flask was charged with sodium hydride (60% oil dispersion 300 mg, 7.5 mmol) which was then washed with hexanes before the addition of butanol (10 mL) containing (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (800 mg, 3 mmol) from Example 4. The solution was stirred at reflux for 2 hours and then neutralized by the addition of 1.0 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanol-chloroform; (810 mg, 94%). Crystallization of such a sample from ethanol/acetonitrile gave an off-white powder, m.p. 122-123° C.

Provenance & Evidence