3-(Pyridin-3-yl)propanal → (+/-)-1-[1-(Biphenyl-4-yloxy)-cyclopropyl]-3-pyridin-3-yl-propan-1-ol

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반응 단계

Lithium naphthalenide (0.625M, 7.4 ml; prepared by adding equimolar quantities of naphthalene and lithium metal to tetrahydrofuran, under nitrogen, and stirring at room temperature overnight) was added slowly to a stirred solution of 4-(1-phenylsulfanyl-cyclopropoxy)biphenyl (0.7 g) in dry tetrahydrofuran at −78° C., under nitrogen, and then stirred at this temperature for 15 minutes. To this was added a solution of 3-pyridinepropanal (0.3 g, prepared according to the method of Example 3 of International Patent Application No. WO-A-92/19593) in dry tetrahydrofuran (15 ml), and the stirring was continued at −78° C. for 5 minutes, then allowed to warm up to room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution, and extracted into diethyl ether (3×30 ml). The combined extracts were washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a pale yellow gum, which was further purified by reverse phase HPLC to give the title compound as a pale yellow gum (0.11 g).

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