Chemical and Pharmaceutical Bulletin p. 2353 - 2357 (1992)
Update date:2022-08-04
Topics:
Fuji
Muratake
Akiyama
Natsume
A new, short-step synthesis of a β-adrenergic blocking agent, pindolol, 1-(4-indolyloxy)-3-(2-propylamino)-2-propanol, is described. The acid-catalyzed indole cyclization reaction of 4-[1-(4-methylphenyl)sulfonyl-3-pyrrolyl]-4-oxobutanal (14) in the presence of (±)-3-chloro-1,2-propanediol (12) and (R)-1-O-[(4-methylphenyl)sulfonyl]glycerol (24) afforded (±)-1-chloro-3-[1-(4-methylphenyl)sulfonyl-4-indolyloxy]-2-propanol (15) and (R)-(-)-3-[1-(4-methylphenyl)sulfonyl-4-indolyloxy]-1-[(4-methylphenyl sulfonyloxy]-2-propanol (25). Reaction of these with isopropylamine and removal of the protecting group at the indole nitrogen gave (±)- and (S)-(-)-pindolol (3 and 4), thus constituting an efficient three-step synthesis of 3 and 4 from the readily available aldehyde (14).
View MoreSICHUAN TONGSHENG AMINOACID CO.LTD
website:http://www.aminoacid.cc
Contact:86-838-2274206/2850606
Address:Room 1-11-1,No.19 of North TianShan Road,Deyang,Sichuan China
Feis International Trade Co,. Ltd
Contact:13961823444-18235944442
Address:Wuxi jiangsu
Contact:0792-8228321
Address:10TH Floor No.121 binjiang Road Xunyang District
Jiangxi Dongxu Chemical Science & Technology Co.,Ltd
Contact:+86-791-86899381
Address:Nanchang, Jiangxi, China
Zhejiang Newfine Industry Co.,Ltd.
Contact:+86-573-82262042
Address:No.225,Dongqing Road, garoms@163.com
Doi:10.1021/jo00050a013
(1992)Doi:10.1002/chem.201204076
(2013)Doi:10.1246/cl.1992.1401
(1992)Doi:10.1016/j.poly.2013.04.026
(2013)Doi:10.1002/anie.201205823
(2012)Doi:10.1016/j.tetlet.2013.09.130
(2013)