4-Methylmorpholine → 4-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

1.30 g (5.0 mmol) of 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid [U.S. Pat. Appl. Publ. (2005), 89 pp. US 2005096337 A1] and 0.969 g (5.25 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine were dissolved under argon in 5 mL of MeCN and cooled down to 0° C.; then, 1.10 mL (1.064 g=2.0 eq.) of N-methylmorpholine was added and the mixture was stirred at 0° C. for 2 h. To this mixture was added 1.277 g (6.0 mmol) 4-amino-piperidine-carboxylic acid tert-butyl ester in small portions; afterwards the reaction was then warmed up to rt. After stirring for 16 h, it was poured into crashed ice and extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. to yield 2.18 g of the crude title compound as off-white solid. MS: 435.2 (MH+).

Provenance & Evidence