Ethyl Acetate → 8-[(1H-Inden-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

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Reaction Steps

Crude 8-(1H-inden-2-ylcarbonyl)-1-phenyl-1,3,8-triazaspiro-[4.5]decan-4-one (11.4g) is dissolved in dry pyridine (250 ml), treated with sodium borohydride (6.0g), and the resulting mixture is refluxed for 16 hours under a nitrogen atmosphere. The pyridine solution is cooled, poured into 2 liters of ice water, stirred for 1 hour and the precipitates filtered off. The crude product is dissolved in chloroform and washed with water and saturated sodium bicarbonate solution. Concentration of the dried chloroform solution gives a crude solid which is a mixture of compounds. Column chromatography through silica gel using ethyl acetate followed by high pressure liquid chromatography with 4:1 ethyl acetate/hexane gives 1.3g of the title compound, melting point 184°14 186° C.

Provenance & Evidence