539-15-1Relevant articles and documents
THE BIOSYNTHESIS OF SCELETIUM ALKALOIDS IN SCELETIUM SUBVELUTINUM
Herbert, Richard B.,Kattah, Abdullah E.
, p. 141 - 144 (1989)
Six Sceletium (Mesembrine) alkaloids (1)-(6) are identified, together with N,N-dimethyltyramine (10) as constituents of Sceletium subvelutinum.The alkaloids (1)-(6) incorporate label from radioactive tyramine (8) and 4-hydroxyphenylpropionic acid (12) as expected; notably -4-hydroxydihydrocinnamaldehyde is a more efficient alkaloid precursor than the acid (12).Preliminary evidence locates the amine (16) potentially as a key precursor for Sceletium alkaloids; (14) is less efficiently incorporated.
STRUCTURE OF THE NEW DITERPENE ALKALOID ZERACONINE AND ITS N-OXIDE
Vaisov, Z. M.,Yunusov, M. S.
, p. 337 - 338 (1987)
The structures of the new diterpene alkaloid zeraconine and its N-oxide, isolated from Aconitum zeravschanicum, have been established on the basis of spectral characteristics and chemical transformations.
Preparation method of hordenine hydrochloride
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Paragraph 0042-0045, (2021/11/10)
The invention discloses a preparation method of hordenine hydrochloride. The preparation method comprises the following steps: taking 4-(2-bromoethyl)phenol as a raw material, adding ethanol to prepare a solution, dropwise adding excessive dimethylamine solution, and stirring at a lower temperature to carry out amination reaction to obtain hordenine hydrobromide. The proper excessive dimethylamine is adopted, so that the quaternization side reaction is effectively inhibited, the solvent dispersion effect is also played, the contact reaction opportunity of the hordenine product generated in the first reaction and the 4-(2-bromoethyl)phenol added later is greatly reduced, the high product yield can be kept, and meanwhile the low preparation cost is achieved; 4-(2-bromoethyl) phenol is added into ethanol to prepare a dilute solution of ethanol, and the dilute solution of ethanol is dropwise added into a dimethylamine solution to improve the dispersity of 4-(2-bromoethyl) phenol in a reaction system and inhibit quaternization side reaction; and the amination reaction is carried out by stirring at a relatively low temperature of 10-25 DEG C, so that the occurrence of quaternization side reaction is inhibited, and a relatively good reaction effect is achieved.
Commercial Pd/C-Catalyzed N-Methylation of Nitroarenes and Amines Using Methanol as Both C1 and H2 Source
Goyal, Vishakha,Gahtori, Jyoti,Narani, Anand,Gupta, Piyush,Bordoloi, Ankur,Natte, Kishore
, p. 15389 - 15398 (2019/12/04)
Herein, we report commercially available carbon-supported-palladium (Pd/C)-catalyzed N-methylation of nitroarenes and amines using MeOH as both a C1 and a H2 source. This transformation proceeds with high atom-economy and in an environmentally friendly way via borrowing hydrogen mechanism. A total of >30 structurally diverse N-methylamines, including bioactive compounds, were selectively synthesized with isolated yields of up to 95%. Furthermore, selective N-methylation and deuteration of nimesulide, a nonsteroidal anti-inflammatory drug, were realized through the late-stage functionalization.
Selective Monomethylation of Amines with Methanol as the C1 Source
Choi, Geunho,Hong, Soon Hyeok
supporting information, p. 6166 - 6170 (2018/04/30)
The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.
