Boron Analogues of Choline. 2.1 Efficient Syntheses of Boron Analogues of Choline, Acetylcholine, and Substituted Acetylcholines

An efficient synthesis of isoelectronic and isostructural boron analogues of acetylcholine [CH3C(0)0CH2CH2N(Me2)BH3], benzoylcholine, (phenylacetyl)choline, and (phenoxyacetyl)choline from the reaction of the corresponding ester hydrochlorides with Et4NBH4 is described. The ester hydrochlorides are prepared from Me2NCH2CH2OH and the corresponding acid chlorides. Both reactions are very mild and give almost quantitative yields of products. A boron analogue of choline is similarly prepared from Me2NCH2CH2OH•HCl, which is in turn made efficiently from dimethylethanolamine and anhydrous HC1. ((Trimethyl-amine-boryl)carbonyl)choline is prepared by condensing trimethylamine-carboxyborane and the boron analogue of choline with dicyclohexylcarbodiimide. A boron analogue of suberoyldicholine is prepared from the reaction of the corresponding diester hydrochloride with NaBH4. © 1986, American Chemical Society. All rights reserved.

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Author Andrew T. McPhail Chemistry