Water → HCID 67385631, compound

Participants

Reaction Steps

A solution of compound racemic 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (2.5 g, 8.77 mmole) in 10 mL of DMF was added at 0° C. to a stirred suspension of NaH 60% dispersion in oil (355 mg, 8.77 mmole) in 10 mL of DMF. The reaction mixture was allowed to stir RT for one hour before being cooled to 0° C. Methyl iodide (1.37 mL, 21.92 mmole, 2.5 eqv) was added slowly and the reaction mixture was stirred at RT for 3 h before being poured into cold H2O and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried, and evaporated to give 2.5 g of 4-methyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester desired compound (95% yield).

Provenance & Evidence