Amantadine → HCID 22816336, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere 6.5 ml of isobutylchloroformate is added to 100 ml of a stirred methylene chloride solution containing 2 g of 5A sieves, 13.26 g Boc-phenylalanine, and 5.5 ml of N-methylmorpholine at -50° C. Over a 30 minute period the reaction mixture is warmed to -10° C. and then recooled to -40° C., and 7.94 g of 1-aminoadamantane is added. The cooling bath is removed, and the reaction mixture is stirred at room temperature overnight. The solution is filtered and washed with 50 ml of cold 1 M potassium bisulfate solution followed by washes with 20 ml portions of 2 M potassium carbonate solution and saturated sodium chloride solution. The solution is then dried over sodium sulfate, filtered and concentrated to dryness to give Boc-L-phenylalanyl-1-aminoadamantane which is represented by the following formula ##STR32##

Provenance & Evidence