8-(4-Tert-butoxycarbonyl-piperazin-1-yl)-6-chloro-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid benzyl ester → 4-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

A solution of 8-(4-tert-butoxycarbonyl-piperazin-1-yl)-6-chloro-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid benzyl ester (640 mg, 1.32 mmol) in ethanol (10 mL) was hydrogenated at 50 psi in the presence of palladium on carbon for 12 hours. The catalyst was removed by filtration, and the filtrate was concentrated to give 4-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester as a light yellow solid (350 mg, 84%). MS: MH+=320.

Provenance & Evidence