350508-55-3

Upstream product

• 55179-51-6 (-)-aminomenthol 
• 334706-50-2 2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 203190-43-6 N-(o-bromobenzyl)-8-aminomenthol 
• 104-55-2 3-phenyl-propenal 
• 350508-50-8 N-(o-bromobenzyl)-2α-styryl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 

Downstream Products

• 350508-65-5 (1R,2S,5R)-2-[1-((3S,4R)-4-Benzyl-3-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 
• 350508-66-6 (3S,4R)-4-benzyl-3-methyl-3,4-dihydroisoquinoline 
• 350508-59-7 (1R,2S,5R)-2-[1-((R)-4-Benzyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol 

Relevant academic research and scientific papers

Synthesis of enantiopure mono- and disubstituted tetrahydroisoquinolines by 6-exo radical cyclizations

2-(o-Bromophenyl)-3-allyl- and 2-allyl-3-(o-bromobenzyl)-substituted perhydrobenzoxazines, derived from (-)-8-amino menthol, readily cyclized stereoselectively by reaction with tributyltin hydride in the presence of AIBN. The cyclization compounds were transformed into enantiopure 4-alkyl tetrahydroisoquinolines by reductive ring opening of the N,O-acetal moiety with lithium aluminum hydride. Enantiopure 1,4- and 3,4-dialkyl-substituted tetrahydroisoquinolines were also prepared by reaction of the cyclized compounds with methylmagnesium iodide and subsequent elimination of the menthol appendage.