10.1039/jr9300002674
The study investigates the synthesis, resolution, and properties of optically active diphenylhydroxyethylamines and their derivatives. The researchers synthesized di-p-methoxyphenylhydroxyethylamine and di-3:4-methylenedioxyphenylhydroxyethylamine by condensing glycine with anisaldehyde and piperonal respectively. These compounds were then resolved into their optically active components using fractional crystallization of their hydrogen d-tartrates. The study also explored the reaction of these bases with nitrous acid, resulting in the formation of a substituted ethylene oxide in the case of di-p-methoxyphenylhydroxyethylamine, which was found to be optically inactive and highly stable. Various derivatives of the synthesized compounds, such as hydrochlorides, monoacetyl and diacetyl derivatives, benzylidene derivatives, and quaternary ammonium iodides, were prepared and characterized. The study provides a detailed comparison of the physical properties of these bases and their derivatives, highlighting the enhancement of rotatory power due to substitution in the aromatic nuclei.
10.1021/ja01649a029
The research aims to explore the synthesis of dimethyl-(α-hydroxy-β-propiothetin) hydrochloride (IIb) and related compounds as part of a broader study on sulfonium compounds as potential lipotropic agents. The researchers used various routes to synthesize IIb, including reactions of dimethyl sulfide with epoxides and acid-catalyzed reactions with lactones. Key chemicals involved include dimethyl sulfide, hydrogen chloride, ethylene oxide, potassium glycidate, ethyl glycidate, and methyl glycidate. The study found that while sulfonium compounds could be obtained from these reactions, yields were generally low (10 to 20%), likely due to competing reactions such as epoxide ring cleavage by hydrogen chloride. The researchers also synthesized related compounds like sulfocholine hydrochloride (IIa), (2-hydroxy-2-carbethoxy)-ethyldimethylsulfonium chloride (IIc), and (1,1-dimethyl-2-hydroxy-2-carbomethoxy)-ethyldimethylsulfonium chloride (IId) through similar methods. The study concludes that while the synthesis of these compounds is feasible, improving yields remains a challenge, and further research is needed to optimize the reaction conditions and explore alternative synthetic routes.
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