Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1982-04-26
1987-04-14
Hines, Robert V.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
26056118, 564304, C07C10329
Patent
active
046580603
ABSTRACT:
There is disclosed a multistep process for producing (-)-5-[(R)-1-hydroxy-2-((R)-1-methyl-3-phenyl-propyl)aminoethyl]salicylami de in high yields which does not require chromatography.
The process is stereoselective for the desired products starting with the reaction of D-(+)-alpha-methylbenzylamine with benzylacetone followed by reduction of the resulting Schiff's base to form an amine as an R,R: R,S diastereomeric mixture, resolution of the mixture to obtain the R,R stereoisomer as a salt, conversion to a free base, reaction of the R,R free base with an O-protected alpha-bromo-3-carbamoyl-acetophenone to produce the corresponding R,R-ketobenzamide, reduction to produce a mixture of S,R,R;R,R,R hydroxybenzamide, removal of the protecting groups, resolution of the deprotected product and then conversion to the free R,R-amine.
REFERENCES:
patent: 4000197 (1976-12-01), Barfknecht et al.
patent: 4012444 (1977-03-01), Lunts et al.
patent: 4101579 (1978-07-01), Hartley et al.
patent: 4137328 (1979-01-01), Cox et al.
patent: 4173583 (1979-11-01), Gold et al.
Babad Esther
Chang Wei K.
Gold Elijah J.
Peer Lydia
Hines Robert V.
Magatti Anita W.
Rosen Gerald S.
Schering Corporation
LandOfFree
Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-pheny does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-pheny, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-pheny will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1787147