4-Methylmorpholine → 4-[N'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

2.2 g (6.22 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid hydrazide from step b were suspended in 15 ml of DMF together with 1.43 g (6.22 mmol) of 1-Boc-piperazine-4-carboxylic acid (preparation analogous to Bioorganic & Medicinal Chemistry Letters, 2001, vol. 11, #24 p. 3161-3164), 2.41 g (12.45 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 867 mg (6.22 mmol) of 1-hydroxybenzotriazole hydrate. 1.40 ml (12.45 mmol) of 4-methylmorpholine were added to the reaction mixture, which was then stirred at room temperature overnight, stirred into 350 ml of water. The resultant precipitate was filtered off with suction, dissolved in DCM, dried, stripped off to dryness and purified by means of flash chromatography on silica gel.

Provenance & Evidence