Water → (1S, 2R)-1-phenyl-2-hydroxymethylcyclopropane N,N-diethylcarboxamide

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Reaction Conditions

Reaction Steps

1.7 ml (16 mmol) of diethylamine was dissolved in 20 ml of anhydrous tetrahydrofuran. To the resultant solution was dropwise added 11 ml (16 mmol) of a solution of 1.64M butyllithium in hexane in a stream of argon gas at 0° C., to thereby obtain a solution of lithium diethylamine. To the obtained solution was dropwise added a solution of 1.7 g (10 mmol) of compound 25 obtained in Reference Example 17 in 20 ml of anhydrous tetrahydrofuran in a stream of argon gas at -78° C. to thereby obtain a mixture. Then, the obtained mixture was stirred at -78° C. for 2 hours to thereby effect a reaction. To the obtained mixture was added a saturated aqueous ammonium chloride solution to thereby terminate the reaction and then, the resultant mixture was subjected to distillation under reduced pressure to thereby remove the solvent and obtain a residue. Water was added to the obtained residue, and ethyl acetate was further added for extraction to obtain an organic layer. The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography (the composition of the developing solvent was; ethyl acetate:hexane=1:1). As a result, compound 26 (yield: 88%) was obtained as a yellow oily product.

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