Spiro[indene-1,4'-piperidine] → 1''N-(2-adamantyl)spiro[1H-indene-1,4''-(hexahydropyridine)]-1''-carboxamide

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Reaction Steps

Spiro(1H-indene-1,4'-piperidine) (20 mg, 0.108 mmol) and 2-adamantyl isocyanate (18 mg, 0.10 mmol) were combined in CH2Cl2 and stirred overnight at ambient temperature. An additional 5 mg (0.028 mmol) of 2-adamantyl isocyanate and 2 drops of triethylamine were added and the mixture again stirred overnight at ambient temperature. The mixture was chromatographed directly on a silica gel column eluted with CH2Cl2 followed by 0.5% and 1% methanol in CH2Cl2. The product fractions were combined and evaporated to dryness in vacuo, and the residue was crystallized from petroleum ether to provide the title compound as a solid: (mp 189°-191°).

Provenance & Evidence