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With 18-crown-6 ether; sodium hydride In N,N-dimethyl-formamide at 25℃; for 4 h;
Synthesis of Amine Building Block A-064-[4-(3-Pyrrolidin-1-yl-propyl)-piperidin-4-yl]-pyridine trihydrochloride (A-06) Step-1: To a THF solution (72 ml) of 4-pyridyl acetate (4 g) was added bis-(2-chloro-ethyl)-carbamic acid tert-butyl ester (3 eqv), NaH (3 eqv), 18-crown-6 (0.4 eqv) and DMF (10 ml) at 25° C. and the resulting reaction mixture was allowed to stir at same temperature for 4 hrs (monitored by TLC). Reaction was cooled to 0° C., quenched with crushed ice and diluted with ethyl acetate. Organic layer was washed successively with water and brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product which was purified by column chromatography. Yield: 67percent
A. 4-Pyridineethanol Fifteen grams (0.091 mol) of 4-pyridineacetic acid ethyl ester was dissolved in 180 ml of dry THF. The solution was transferred to a 1 l., 3-neck round bottom flask which had been flushed with nitrogen. To the mixture was added dropwise 55 ml of 1.0 M lithium aluminum hydride (0.055 mol) at approximately 0 C. The reaction mixture became yellow upon addition of the reducing agent. Following addition, the mixture was quenched with 2.1 ml of water at 0 C. followed by 2.1 ml of 15% by volume of sodium hydroxide and 6.3 ml of water. The mixture was allowed to stir at room temperature for approximately 4 hours and filtered through Celite. The filtrate was concentrated under vacuum to provide 6.38 g of 4-pyridineethanol. This material was used directly in the following reaction.
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