321670-13-7

Basic information

• Product Name: (1R)-N-(8-menthyl)-1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (1R)-N-(8-menthyl)-1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 321670-13-7
• Molecular Weight: 497.675
• Mol File: 321670-13-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R)-N-(8-menthyl)-1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-N-(8-menthyl)-1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(321670-13-7)
• EPA Substance Registry System: (1R)-N-(8-menthyl)-1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(321670-13-7)

Safety Data

• Hazardous Substances Data: 321670-13-7(Hazardous Substances Data)

Upstream product

• 321669-63-0 2α-(2'-bromo-4',5'-dimethoxyphenylmethyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 321669-67-4 N-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-8-aminomenthol 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 55171-60-3 2-bromo-3,4-dimethoxybenzylaldehyde 
• 321669-90-3 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(3',4'-dimethoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 55179-51-6 (-)-aminomenthol 
• 90841-59-1 2-(2-bromo-4,5-dimethoxyphenyl)acetaldehyde 

Downstream Products

• 50896-90-7 (-) N-norlaudanosine 
• 85-63-2 (R)-laudanosine 

Relevant articles and documents

A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids

A novel, direct, and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes.