Asymmetric reactions. XXIX. Absolute configuration of ω-phenyl-2-alkylamines and their N-methyl derivatives

Abstract

Absolute configuration of ro-phenyl-2-alkylamines Ia -Ic (R = H) and their N-methyl derivatives la-Ie (R = CH 3 ) has been determined by the method of the asymmetric transformation and analysis of ORD curves. In the case of the amine Ic (R = H) also the chemical corr.elation has been used.In connection with the use of the asymmetric transformation in determining the absolute configuration of organic compounds 1 -3, the absolute configuration of co-phenyl-2-alkylamines la-Ie (R = H) and their N-methyl derivatives la-Ie (R = CH 3 ) has been determined. In molecules of these amines, the aromatic ring is separated in a various distance from the asymmetric carbon atom by a saturated chain. It was therefore of interest to measure the 0 RD curves of these compounds and to determine the influence of the aromatic chromophore on the shape and sign of the Cotton effect while the absolute configuration is equal.

Reductive Amination in the Synthesis of Pharmaceuticals

“…An example of the synthesis of evekeo using the Leuckart reaction is described in the work of C ̌ervinka. 136 The authors used ammonium formate as a source of nitrogen and hydrogen to obtain racemic evekeo 2.26.1 (18.5 g) in 41% yield and with 16% RME.…”

“…Methyl benzyl ketone 2.26.a was heated either with ammonium formate or with formamide to form evekeo or formamide 2.26.c , which was hydrolyzed to form the required product. An example of the synthesis of evekeo using the Leuckart reaction is described in the work of Červinka . The authors used ammonium formate as a source of nitrogen and hydrogen to obtain racemic evekeo 2.26.1 (18.5 g) in 41% yield and with 16% RME.…”

The DARK Side of Total Synthesis: Strategies and Tactics in Psychoactive Drug Production

“…For example, in 1968, Belovsky and co-workers demonstrated a simple synthesis of (±)-amphetamine ( 123 ) from phenylacetone ( 151 ) and formamide (Scheme 23). 83 The synthesis began with the condensation of phenylacetone ( 151 ) and formamide under Leuckhart conditions to give (±)- 152 . Subsequent hydrolysis yielded (±)-amphetamine ( 123 ), completing the synthesis in two simple transformations.…”

“…From this research, compounds like fentanyl (84) emerged. While all of the opioids are addictive, some are larger targets for abuse such as Demerol (83) and methadone (85), while others are less abused due to their high potency and increased likelihood for overdose.…”

(S)-α-Methyl-N-(phenylmethyl)benzenepropanamine hydrochloride[(S)-N-benzyl-1-methyl-3-phenylpropylamine hydrochloride]: determination of absolute configuration

“…The resolution of racemic 1-methyl-3-phenylpropylamine has been reported on three occasions by Dutch ( van Dijk, Keizer & Moed, 1963), Russian (Potapov, Dem'yanovitch & Terent'ev, 1964), and Czech (Cervinka, Kroupova & Belovsky, 1968) workers. The Dutch and Czech groups attempted to establish the absolute configuration of the (+)-enantiomer by degradation to compounds with known absolute configuration but they arrived at opposite conclusions.…”