31925-54-9

Upstream product

• 76497-43-3 (R,S)-N-methyl-β-phenyl-β-alanine 
• 107-13-1 acrylonitrile 

Downstream Products

• 88931-10-6 (R,S)-N-(2-aminopropyl)-N-methyl-β-phenyl-β-alanine 
• 31948-95-5 3-[(2-Cyano-ethyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-64-1 3-[(3-{3-[(2-Cyano-ethyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-65-2 3-[(3-{3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-67-4 3-[(3-{3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid 
• 32063-92-6 3-[(3-Benzyloxycarbonylamino-propyl)-methyl-amino]-3-phenyl-propionic acid 
• 31925-63-0 3-[(3-Benzyloxycarbonylamino-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31948-96-6 3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 88931-12-8 (R,S)-5-methyl-4-phenyl-1,5-diazacyclooctan-2-one 
• 88909-11-9 (R,S)-1-(4-chlorobutyl)-5-methyl-4-phenyl-1,5-diazacyclooctan-2-one 
• 20410-93-9 1,1'-(butane-1,4-diyl)bis[hexahydro-5-methyl-4-phenyl-1,5-diazocin-2(1H)-one] 

Relevant academic research and scientific papers

Synthesis of the Alkaloid Homaline in (+/-) and Natural (S,S)-(-) Forms, using Amination and Transamidative Ring Expansion in Liquid Ammonia

Synthesis of the alkaloid homaline in (+/-) and natural (S,S)-(-) forms is reported.Linking of 2-azacyclooctanone units either directly or successively using 1,4-dihalogenobutanes or 1,4-dihalogenobut-2-ynes is examined. (+/-)-5-Methyl-4-phenyl-1,5-diazacyclooctan-2-one is first made by a 2,2'-dithiodipyridine/triphenylphosphine-mediated cyclisation, and then by amination and transamidative ring expansion from N-(3-chloropropyl)-4-phenylazetidin-2-one in liquid ammonia, followed by N-methylation.Coupling through a 1,4-dihalogenobutane of either the N-methylated azalactam, or the unmethylated azalactam followed by methylation, gave homaline in (+/-) and meso forms. (R)-(-)-Phenylglycine was converted via (S)-β-phenyl-β-alanine into an (S)-β-lactam which was then alkylated with 1-bromo-3-chloropropane, and aminated and ring expanded in liquid ammonia.Coupling of the homochiral azalactam (2 mol) so formed with 1,4-dibromobutane, followed by N-methylation, gave (S,S)-(-)-homaline identical with the natural material.