1-(4-Chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione → 1-(4-Chlorobenzyl)-7-cyclohexyl-3-hydroxy-3-methyl-1,7-diazaspiro[4.4]nonan-6-one

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2-Methylallylmagnesium chloride in THF (3.0 M, 0.074 mL) was added to a solution of 1-(4-chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione (0.040 g, 0.00011 mol) in THF (1.0 mL, 0.012 mol) and the resulting mixture was stirred at 50° C. for 1 h. The reaction mixture was then allowed to cool to RT and was then quenched by the addition of saturated NH4Cl. The crude reaction mixture was purified by prep. HPLC to afford the desired product. LC/MS: 377.2 (M+1H)+.

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