Phenylephrine hydrochloride, SLV-325, Incostop, Neo-Synephrine hydrochloride, Nostril, Mydfrin, Biomydrin, Alcon Efrin

盐酸去氧肾上腺素 去氧肾上腺素 Chemical Name: (-)-3-[1(R)-Hydroxy-2-(methylamino)ethyl]phenol hydrochloride
CAS No. 61-76-7, 59-42-7 (free base)
项目整合开发状态: Launched
项目研究机构: Solvay (Marketer), SLA Pharma (Licensee)
合成路线:3-Hydroxybenzaldehyde (I) was protected as the methoxyethoxymethyl ether derivative (II) by treatment with methoxyethoxymethyl chloride and diisopropyl ethyl amine.Subsequent condensation of (II) with dimethyloxosulfonium methylide,generated from oxosulfonium salt (III) and NaH,gave rise to the racemic epoxide (IV).Kinetic resolution by hydrolysis with (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt (III) acetate complex provided the (S)-diol (V) along with the unreacted (R)-epoxide (VI),which were separated by column chromatography.Opening of the desired (R)-epoxide (VI) with methanolic methylamine gave amino alcohol (VII).Finally,removal of the methoxyethoxymethyl group by refluxing in methanolic HCl furnished the title compound.