Diisopropylamine → (+/-)-3-(1,2-dihydro-1-hydroxy-2,2-dimethyl-1-acenaphthylenyl)-N,N-bis(1-methylethyl)-4-pyridinecarboxamide

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Reaction Conditions

Reaction Steps

Preparation of: ##STR30## To a cooled (-80° C.) and stirred solution of 5.25 g of N-(1-methylethyl)-2-propanamine in 500 ml of dry tetrahydrofuran there were added 20 ml of butyl lithium (2.5M in hexane) and, after stirring for 1 hour at -80° C., 10.3 g of N,N-bis(1-methylethyl)-4-pyridinecarboxamide (prepared as described in Tetr. Lett. 21, 4739, 1980). Stirring at -80° C. was continued for 3 hours and then there were added 9.3 g of 2,2-dimethylacenaphthylen-1(2H)-one. The whole was stirred for 18 hours at room temperature and was then poured into water. The product was extracted with ether and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated, yielding 4.2 g (20.9% ) of (±)-3-(1,2-dihydro-1-hydroxy-2,2-dimethyl-1-acenaphthylenyl)-N,N-bis(1-methylethyl)- 4-pyridinecarboxamide (comp. 5.006)

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