Water → 3-(Pyrrolidin-1-yl)-4,5-dihydroisoxazole

Participants

Reaction Conditions

Reaction Steps

3-(Pyrrolidin-1-yl)-4,5-dihydroisoxazole III-59 was prepared in 1 step according to the following procedure: 3-bromo-4,5-dihydroisoxazole III-18 (1.0 equiv) was dissolved in n-butanol (0.64 M) followed by the addition of pyrollidine (1.2 equiv) and sodium carbonate (2.5 equiv). The reaction is the sealed and heated in an oil bath to 120° C. for 18 h after which it allowed to cool and then transferred to a separatory funnel with excess water and tert-butylmethyl ether. The aqueous layer was washed with tert-butylmethyl ether (2×) and the combined organic layers were washed with brine, dried over magnesium sulfate and concentrate to provide a orange solid that was purified using flash silica gel chromatography (gradient ethyl acetate/hexanes) to provide III-59 as a white solid. [M+H]+=345.4 m/z. Activity: C

Provenance & Evidence