Directional nature of hydrophobic bonding in phenethanolamine N-methyl transferase inhibitors

Abstract

Notes (0.35 mm) [lit.9 73°,(2.0 mm), 37% yield by Na reduction],Trans Esters. The trans esters in Table I were all prepd in the usual manner by addn of the acid chloride in PhH to the alcohol and Et3N in PhH. Nmr (CDC13) spectra of all trans esters were similar to that of the alcohol. Under triple irradiation, decoupling both CH2 groups, the vinyl protons of the morpholino pivalate appeared as a singlet (half-bandwidth 3 Hz).4-Amino-2-butyn-l-ol Esters. The esters in Table II were prepd as above for the trans esters from the corresponding alcohol and acid chloride.Cis Esters. The cis esters in Table I were prepd by redn with H2 and 5% Pd/C in EtOH at room temp and atm pressure to the theoretical amt. Usual work-up and distn; nmr (CDC13) 6.04 (octet, 2, half-bandwidth ~28 Hz). Triple irradiation, as above, showed a quartet (/ab =11.5 Hz).