新产品编号:511495

Chemical Name: N-Ethyl-N-[1-[4-hydroxy-3-[N-methyl-N-(phenylsulfonyl)aminomethyl]-3-phenylbutyl]piperidin-4-yl]carbamic acid benzyl ester enantiomer A
CAS No. 220394-36-5 ((R)-isomer), 220394-35-4 ((S)-isomer), 220394-27-4 (undefined isomer)
项目整合开发状态: Biological Testing
项目研究机构: Merck & Co. (Originator)
合成路线:The alkylation of 2-phenyl-4-pentenenitrile (I) with 2-(trimethylsilyl)ethoxymethyl chloride (II) in the presence of LDA afforded (III),which was reduced to aldehyde (IV) by means of DIBAL.Reductive amination of (III) with methylamine and NaBH(OAc)3 produced amine (V) and subsequent condensation with benzenesulfonyl chloride (VI) yielded sulfonamide (VII).A two-step oxidation of (VII) with osmium tetroxide and N-methylmorpholine-N-oxide,followed by sodium periodate cleavage of the resulting diol (VIII) generated aldehyde (IX).Further reductive amination of (IX) with piperidine derivative (X) gave adduct (XI).The (trimethylsilyl)ethoxy protecting group of (XI) was finally cleaved by means of trifluoroacetic acid to furnish the title compound.