Ammonium formate → tert-Butyl 5-oxa-2,8-diazaspiro[3.5]nonane-8-carboxylate

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Reaction Steps

A mixture of tert-butyl 2-benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonane-8-carboxylate (0.85 g) (example 176 step b), ammonium formate (0.883 g) and palladium on carbon JM type 87 L (0.459 g) in ethanol (50 mL) was refluxed for 30 minutes. The mixture was cooled to RT and filtered through celite, the solvent was evaporated under reduced pressure. The celite pad was washed with 10 mL of DMF) and then with 50 mL of acetonitrile. These washings were used to dissolve the residue obtained from evaporation of the initial mixture. This solution was passed through a 10 g SCX cartridge, followed by washing with acetonitrile. The cartridge was the eluted with a 10% solution of 880 ammonia in acetonitrile (80 mL) to bring off product. The solvents were evaporated under reduced pressure and the residue diluted with acetonitrile and evaporated under reduced pressure to afford the subtitled compound. Yield 0.490 g.

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