Acetylene → 1-Azabicyclo[2.2.2]oct-3-yl 2-hydroxy-2-phenyl-3-butynoate

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Reaction Steps

The above ester (13.0 g., 0.5 mole) was dissolved in 500 ml. of THF, cooled to 5° in an ice bath and treated, dropwise with a THF solution of ethynylmagnesium bromide prepared by known procedures from magnesium (1.3 g., 0.055 g. atom), ethyl bromide (5.5 g., 0.05 mole) and excess acetylene. The reaction mixture was stirred at room temperature for 23 hours, and then poured onto 100 ml. of cold water containing 20 g. of ammonium chloride. The mixture was extracted with ether and then with chloroform. The organic extracts were combined, dried and subsequently stripped of volatile components in vacuo to yield 12.0 g. of oil. The product (3.6 g., 25%) was precipitated from the oil by the addition of ether, and melted at 154°-156° C. after recrystallization from hexane. N.m.r. spectroscopy verified the structural assignments.

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