815. The configuration of noradrenaline

Optical resolution of asymmetric amines by preferential crystallization as lasalocid salts

“…Lasalocid, 6-[7(R)-[5(5)-ethyl-5-(5(R)-ethyltetrahydro-5-hydroxy-6(5)-methyl-2/f-pyran-2(J? )-yl)tetrahydro-3(5)-methyl-2(5)-furyl]-4(5)-hydroxy-3(R),5(5)-dimethyl-6oxononyl]-2,3-cresotic acid (1), was isolated from cultures of 5. lasaliensis as described earlier.2 All the amines are commercially available (Aldrich Chemical Co., Roche Chemical Division, Hoffmann-La Roche Inc., and Norse Laboratories) with the exception of 2-aminol-(3',4'-dimethoxyphehyl)propane (7), which was synthesized as a racemate by Dr. S. Teitel of Hoffmann-La Roche. The TV-trifluoracetyl-L-(5)-prolyl chloride (TPC) reagent was obtained from Regis Chemical Co. as a 0.1 M solution in CHCI3.…”

“…Isolation of (S>(+)-l-Amino-2-(3',4'-dimethoxyphenyl)propane (7) Hydrobromide. The lasalocid salt of 7 with the highest optical purity (80%) was that obtained by recrystallization from ethanol.…”

“…Since norepinephrine (2b) has an asymmetric center (R configuration), the possibility occurred to us that lasalocid might have the ability to resolve racemic amines. The results of attempts to resolve racemic 1-amino-1-phenylethane (3a), 1 -amino-l-(4-bromophenyl)ethane (3b), 1-dimethylamino-1-phenylethane (3d), 1-amino-l-naphthylethane (4), 2-aminoheptane (5), tetrahydrofurfurylamine (6), and 2-aminol-(3',4'-dimethoxyphenyl)propane (7) by crystallization as a salt of 1 from various solvents are given in Table I.…”

The crystal and molecular structure of (±)-octopamine hydrochloride

“…1 and the listed atomic coordinates refer to the enantiomer with the (R)-configuration at the chiral centre, C(7). This corresponds to the configuration of naturally occurring (-)-noradrenaline (Pratesi, La Manna, Campiglio & Ghislandi, 1959), natural (-)-octopamine having the same absolute configuration (Erspamer, 1952;Kappe & Armstrong, 1964).…”

The Basic Constituents of Toad Venoms

“…Also, in an old preparation of adrenaline from Ch'an Su, Lee and Chen (1951) detected noradrenaline pharmacologically. The method employed verifies also that it is the same stereoisomer found in higher animals: R-(-)-noradrenaline (Pratesi et al, 1959).…”