Prenalterol
普瑞特罗Chemical Name: 4-[2(S)-Hydroxy-3-(isopropylamino)propoxy]phenol
CAS No. 57526-81-5, 61260-05-7 (hydrochloride)
项目整合开发状态: Not Determined
项目研究机构:
合成路线:The reaction of 5,6-anhydro-1,2-O-isopropylidene-alpha-D-glucofuranose (I) with monobenzylether of hydroquinone (II) by means of pyridine at 120 C gives 1,2-O-isopropylidene-6-O-(4-benzyloxyphenyl)-alpha-D-glucose (III),which is hydrolized with acetic acid yielding 6-O-(4-benzyloxyphenyl)-alpha-D-glucose (IV).The cleavage of (IV) with NaIO4 in methanol - acetic acid,followed by reduction of the resulting product with NaBH4 in methanol affords 1-(4-benzyloxyphenoxy)-2S-3-dihydroxypropane (V),which is monotosylated with tosyl chloride in pyridine giving the tosyl derivative (VI).The reaction of (VI) with isopropylamine (VII) in hot ethanol affords (S)-3-isopropylamino-1-(4-benzyloxyphenoxy)-2-propanol (VIII),which is finally debenzylated by reduction with H2 over Pd/C in ethanol.
📌 参考资料/链接：
参考文献标题:
文献作者:Schroeter,H.; et al.
参考来源:BE 825289; DE 2503751; FR 2260337; JP 75108228; NL 7501496; ZA 7500799
📄 详细内容
合成路线:The reaction of 5,6-anhydro-1,2-O-isopropylidene-alpha-D-glucofuranose (I) with monobenzylether of hydroquinone (II) by means of pyridine at 120 C gives 1,2-O-isopropylidene-6-O-(4-benzyloxyphenyl)-alpha-D-glucose (III),which is hydrolized with acetic acid yielding 6-O-(4-benzyloxyphenyl)-alpha-D-glucose (IV).The cleavage of (IV) with NaIO4 in methanol - acetic acid,followed by reduction of the resulting product with NaBH4 in methanol affords 1-(4-benzyloxyphenoxy)-2S-3-dihydroxypropane (V),which is monotosylated with tosyl chloride in pyridine giving the tosyl derivative (VI).The reaction of (VI) with isopropylamine (VII) in hot ethanol affords (S)-3-isopropylamino-1-(4-benzyloxyphenoxy)-2-propanol (VIII),which is finally debenzylated by reduction with H2 over Pd/C in ethanol.
参考文献标题:Prenalterol
文献作者:Castar,J.; Weetman,D.F.
参考来源:Drugs Fut 1979,4(1),46
产品链接: CAS No. 57526-81-5›› 产品链接: CAS No.61260-05-7››