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Generated: November 17, 2017

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Title: Novel methods and compounds employed therein
Abstract:Preparation of an optically active alkamine in the sinister configuration, or a derivative of said alkamine, which is reacted with an 3-X-4-chloro(or RO-- where R is hydrogen or an alkali metal)-1,2,5-thiadiazole to prepare S-3-X-4-(3-substituted amino-2-hydroxypropoxy)-1,2,5-thiadiazole beta adrenergic blocking agents. Novel 3-morpholino-4-chloro(or RO--)-1,2,5-thiadiazoles and their preparation also are described.
Inventor(s): Weinstock; Leonard M. (Belle Mead, NJ), Tull; Roger J. (Metuchen, NJ), Mulvey; Dennis M. (Milford, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:Nov 19, 1973
Application Number:05/417,301
Claims:1. A process comprising the reductive alkylation of ammonia, a primary amine or a secondary amine wherein the amine substituents are straight or branched chain lower alkyl groups optionally hydroxy substituted by the dropwise addition of a glyceraldehyde selected from D-glyceraldehyde and isopropylidene-D-glyceraldehyde in the presence of a catalyst selected from platinum, palladium and Raney nickel to provide an S-1,2-dihydroxy-3-amino propane, substantially completely free from its rectus isomer.

2. A process as in claim 1 wherein an amine of the structure YNH.sub.2 is reductively alkylated with D-glyceraldehyde to provide S-1,2-dihydroxy-3-(Y-amino)propane wherein Y is a straight or branched chain lower alkyl optionally hydroxy substituted.

3. A process as in claim 1 wherein an amine of the structure YNH.sub.2 is reductively alkylated with isopropylidene-D-glyceraldehyde to provide S-1,2-dihydroxy-3-(Y-amino)propane wherein Y is a straight or branched chain lower alkyl optionally hydroxy substituted.

4. An optically active glycolamine in the sinister configuration substantially completely free from the rectus isomer having the structure ##EQU7## wherein Y is a straight or branched chain lower alkyl or a hydroxy substituted straight or branched chain lower alkyl.

5. The sinister isomer of 1,2-dihydroxy-3-(Y-amino)propane substantially completely free from contamination with its rectus isomer wherein Y is a straight or branched chain C.sub.1-5 alkyl or a hydroxy substituted straight or branched chain C.sub.1-5 alkyl.

6. S-1,2-dihydroxy-3-tert-butylaminopropane substantially completely free from contamination with its rectus isomer.

7. ##EQU8## substantially completely free from contamination with its rectus isomer wherein Y is straight or branched chain C.sub.1-5 alkyl or hydroxy substituted straight or branched chain C.sub.1-5 alkyl.

8. An optically active glycolamine in the sinister configuration substantially completely free from rectus isomer having the structure ##EQU9## wherein amino is selected from the amino group, monosubstituted amino group and di-substituted amino group wherein the amino group substituents are straight or branched chain lower alkyl optionally hydroxy substituted.
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