Efficient Preparation of (R)- and (S)-2-Amino-1-phenylethanol
Olivier Lohse and Christoph Spöndlin
Chemical and Analytical Development, Novartis Pharma Inc., Building S-145.8.63, CH-4002 Basel, Switzerland
Org. Process Res. Dev., 1997, 1 (3), pp 247–249
DOI: 10.1021/op9600264
Abstract
The preparation of optically pure 2-amino-1-phenylethanol was investigated using three methods. The opening of styrene oxide with ammonia, the reduction of mandelamide, and the resolution of (±)-2-amino-1-phenylethanol were compared from a process R&D viewpoint. The resolution using di-O-p-toluoyltartaric acid was found to be the method of choice and was optimised to yield 62% of optically pure substance.
Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure[BOND]Activity Relationships, Part 3†
Daniel Trachsel
Helvetica Chimica Acta Volume 86, Issue 8, pages 2754–2759, August 2003
DOI: 10.1002/hlca.200390224
STUDIES IN THE PREPARATION OF NITRILES. II. THE PREPARATION OF ALIPHATIC NITRILES.
G. D. van Epps, E. Emmet Reid
J. Am. Chem. Soc., 1916, 38 (10), pp 2120–2128
DOI: 10.1021/ja02267a022
Indolealkylamine and phenalkylamine hallucinogens: Effect of ?-methyl and N-methyl substituents on behavioral activity
Richard A. Glennon
Biochem. Pharmacol. 32 1267 1983
Abstract
Animals (rats), trained to discriminate the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline in a two-lever operant procedure, were challenged with various doses of several indolealkylamine and phenalkylamine derivatives. In both series, the ?-methyl analogs were found to be more active than either their N-methyl or ?-demethyl counterparts. Furthermore, when the activities of the optical isomers of DOM were compared with the activities of S-(+) and R-(?)-?-methyltryptamine (?-MeT), it was found that the more potent isomer of ?-MeT (i.e.S) possessed the opposite absolute configuration of the more potent isomer of DOM (i.e.R). With respect to the mechanism of action of these agents, these findings are not inconsistent with a common site hypothesis.
Olivier Lohse and Christoph Spöndlin
Chemical and Analytical Development, Novartis Pharma Inc., Building S-145.8.63, CH-4002 Basel, Switzerland
Org. Process Res. Dev., 1997, 1 (3), pp 247–249
DOI: 10.1021/op9600264
Abstract
The preparation of optically pure 2-amino-1-phenylethanol was investigated using three methods. The opening of styrene oxide with ammonia, the reduction of mandelamide, and the resolution of (±)-2-amino-1-phenylethanol were compared from a process R&D viewpoint. The resolution using di-O-p-toluoyltartaric acid was found to be the method of choice and was optimised to yield 62% of optically pure substance.
Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure[BOND]Activity Relationships, Part 3†
Daniel Trachsel
Helvetica Chimica Acta Volume 86, Issue 8, pages 2754–2759, August 2003
DOI: 10.1002/hlca.200390224
STUDIES IN THE PREPARATION OF NITRILES. II. THE PREPARATION OF ALIPHATIC NITRILES.
G. D. van Epps, E. Emmet Reid
J. Am. Chem. Soc., 1916, 38 (10), pp 2120–2128
DOI: 10.1021/ja02267a022
Indolealkylamine and phenalkylamine hallucinogens: Effect of ?-methyl and N-methyl substituents on behavioral activity
Richard A. Glennon
Biochem. Pharmacol. 32 1267 1983
Abstract
Animals (rats), trained to discriminate the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline in a two-lever operant procedure, were challenged with various doses of several indolealkylamine and phenalkylamine derivatives. In both series, the ?-methyl analogs were found to be more active than either their N-methyl or ?-demethyl counterparts. Furthermore, when the activities of the optical isomers of DOM were compared with the activities of S-(+) and R-(?)-?-methyltryptamine (?-MeT), it was found that the more potent isomer of ?-MeT (i.e.S) possessed the opposite absolute configuration of the more potent isomer of DOM (i.e.R). With respect to the mechanism of action of these agents, these findings are not inconsistent with a common site hypothesis.