Hydrochloric Acid → HCID 67716932, compound

Participants

Reaction Conditions

Reaction Steps

1.5 g of 3-(R/S)-amino-1-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and 2.23 g of (R)-alpha-[[(4-nitrophenyl)-sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester (Helv. Chim. Acta 71 (2), 337, 1988) are combined and, at 40° C., 0.67 ml of N-methylmorpholine is added. The mixture is heated at 75° C. for 15 h, cooled, diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and water and finally with dilute hydrochloric acid and brine. Flash chromatography (80 g of silica gel, eluant ethyl acetate/hexane 1:2) yields the two diastereoisomers which, after being dissolved in ethyl acetate/tetrahydrofuran, were each converted separately into the corresponding hydrochloride with 3 equivalents of 1N hydrochloric acid. Rf values of the free bases (eluant: ethyl acetate/hexane 1:2):

Provenance & Evidence