Sodium Triacetoxyborohydride is abbreviated as STAB and is also called sodium triacetoxyhydroborate. It is produced by protonolysis and oxidation of sodium borohydride by Acetic acid. It is a reactive agent used in organic syntheses like reductive amination of ketones, aldehydes, aryl aldehydes, and reductive amination/lactonization of carbonyl compounds with amines.
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Properties of Sodium Triacetoxyborohydride
Molecular Formula: C6H10BNaO6
No. CAS: 56553-60-7
Formula weight: 211.94
Density: 0.877 g/ml at 25 degrees Celsius.
Solubility: Soluble in Dimethyl Sulfoxide, methanol toluene, tetrahydrofuran dioxane, and methylene chloride
Arecoline is an alkaloid, natural substance found within the fruits of the Areca palm Areca catechu. The fruit, referred to by the name of betel nuts, is utilized to relax in various Pacific and Asian cultures due to its mild stimulant properties and also for its use in Ayurvedic medical practices and traditional Chinese medicine.
Arecoline is an acetylcholine muscarinic M1 and M2 receptor agonist. It has sparked a moderate amount of interest in academic research on its potential applications in Alzheimer’s disease and other neurodegenerative diseases However, its use is hindered by its known carcinogenicity.
Furthermore, the structure-activity connection of arecoline analogs has been an area of interest for medicinal chemical research. Although arecoline is available commercially and reasonably priced The synthesis described in this paper is an intermediate stage synthesis, as well as the synthesis, is extremely brief and ‘total’. This route utilizes a Fischer esterification N – methylation and semi-reduction using in situ generated sodium triacetoxyborohydride. Arecoline hydrobromide was found to have 11% of the overall yield with nicotinic acid. No attempt was made to maximize yield.
The Fischer isomerization process of nicotinic acids can be accomplished with good results if enough sulfuric acid is present and that the process is permitted to continue for a sufficient amount of time. N-methylation was carried out in a uniform and high yield. While the methods used to prepare N-methyl Pyridinium salts usually require toluene, heating, or both, however, this reaction was discovered to occur in acetone temperatures of room temperature for a period of time.
The subsequent semi-reduction process of this methyl pyridinium salt to tetrahydropyran is been documented with sodium borohydride, in biphasic water/benzene (lit. 42%), though the purported yield with sodium triacetoxyborohydride is higher (lit. 67 percent). Sodium triacetoxyborohydride is a mild reducing agent, and will selectively reduce iminium species and aldehydes.
It is important to note that the pyridinium ions can be regarded as an “ene-iminium” Ion. Upon reduction of the iminium, the enamine will automatize to the iminium, as well as undergo reduction. Sodium borohydride is not expected to provide this selectivity and is more likely to give methyl 1-methyl piperidine-3-carboxylate as a by-product.
The crude 1H-NMR of the triacetoxyborohydride reduction indicated good conversion to product, but fractional crystallization of the product as the hydrobromide salt proved difficult. Modification to this purification procedure will likely increase yield significantly. It is not clear if the salt of hydrochloride is similar to the hydrobromide that is produced in this study. In a small amount, the reduction was observed with a 50% yield isolated.