Enantioselective analysis of methamphetamine (MA) and amphetamine (AP) is necessary in forensic drug analysis. In general, standard materials are required for performing forensic investigation and also for developing new analytical methods. However, l-MA is not commercially available in Japan and only a few reports are available on the enantioselective synthesis of l-MA. We developed a new and convenient method for the synthesis of l-MA using d-norephedrine (d-NE) as a starting material. d-NE was treated with 1,1′ carbonyldiimidazole to produce the corresponding cyclic carbonate, and the product was treated with sodium hydride and iodomethane to form mono-N-methylated amine derivative, which was treated with palladium on activated carbon in hydrogen atmosphere for catalytic reduction. After the addition of aqueous hydrogen chloride (HCl), l-MA was obtained as its HCl salt (total yield 58).
7-Oxocholesteryl hypoiodite in benzene containing mercury(II) oxide and iodine underwent a photo-induced rearrangement to give 5-iodomethyl-A-nor-5ξ-cholestane-3,7-dione and 2-iodo-7-oxo-A-nor-2,3-secocholest-5-en-3-yl formate in low yields, together with cholesta-3,5-dien-7-one without any accompanying 3α,5-epoxy-6-iodo-A-homo-4-oxacholestanes which are common products in the reactions of cholest-5-en-3-ols. The results thus show that the introduction of an oxo group at the C-7 position results in an appreciable change in the products of the reactions of cholest-5-en-3-ols.
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