Nitrogen → 4-[2-(4-tert-Butyl-phenyl)-benzooxazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

4-(3-hydroxy-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.00 g, 3.09 mmol) was charged to a 250 mL round bottom flask containing 10% Pd/C, stir bar and septum. Under a positive stream of N2, 2-propanol (80 mL) was added via syringe. The flask was evacuated and fitted with a balloon containing H2 and stirred, under H2, at room temperature for 18 h. LC-MS indicated only aniline present. 4-tert-Butyl-benzaldehyde (800 μL, 4.64 mmol) was added, the balloon was replaced with an air condenser and the stirring solution was heated to 80° C. for 48 h. The reaction was cooled to room temperature and filtered through celite to remove the catalyst and the solvent removed in vacuo to give a brown oil. This oil was adsorbed onto silica and purified by column chromatography, eluting with 11% ethyl acetate in hexane to afford the product as a clear waxy material (1.09 g, 81%). Mass Spectrum (+ESI): 436 [M+H]+.

Provenance & Evidence