R. B. Walker, W. L. Nelson
1978
Citations
0
Influential Citations
6
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Syntheses of 1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol-1,1,2,3,3-d5 (1), 3-(1-naphthyloxy)-1,2-propanediol-1,1,2,3,3-d5 (2) and 1-(isopropylamino)-3-(4-hydroxy-1-naphthyloxy)-2-propanol-1,1,2,3,3-d5 (3) from epichlorohydrin-d5 are described. Treatment of epichlorohydrin-d5 with 1-naphthol, in the presence of a catalytic amount of pyridine, afforded a mixture of 1-chloro-3-(1-naphthyloxy)-2-propanol-1,1,2,3,3-d5 (4) and 1,2-epoxy-(1-naphthyloxy)-propane-1,1,2,3,3-d5 which was converted to 4, with HCl or to 5 with 6N KOH. Reaction of 4 with isopropylamine afforded 1. Acid catalyzed hydrolysis of 5 afforded 2. A modification of the synthesis of 1 using 4-methoxy-1-naphthol, epichlorohydrin-d5 (1N NaOH) afforded epoxide 7, which was opened with isopropylamine. Ether cleavage with pyridine HCl completed synthesis of 1-(isopropylamino)-3-(4-hydroxy-1-naphthyloxy)-2-propanol-1,1,2,3,3-d5 (3).