60383-76-8

Upstream product

• 72527-29-8 6,7-dimethoxy-1-(4-methoxybenzyl)-3,4-dihydroisoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 41498-37-7 7,12-O,O'-dimethylcoclaurine 
• 321669-88-9 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 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 
• 90841-59-1 2-(2-bromo-4,5-dimethoxyphenyl)acetaldehyde 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 55171-60-3 2-bromo-3,4-dimethoxybenzylaldehyde 
• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 

Downstream Products

• 5701-00-8 (R)-O-methylarmepavine 

Relevant academic research and scientific papers

Synthesis of (-)-(S)-norlaudanosine, (+)-(R)-O,O-dimethylcoclaurine, and (+)-(R)-salsolidine by alkylation of an α-aminonitrile

A short asymmetric synthesis of 1-substituted 1,2,3,4- tetrahydroisoquinoline alkaloids by deprotonation of an unprotected α-aminonitrile and alkylation of the resulting carbanion followed by spontaneous elimination of HCN and asymmetric reduction is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

METHOD FOR RESOLVING ENANTIOMERS FROM RACEMIC MIXTURE HAVING CHIRAL CARBON IN ALPHA POSITION OF NITROGEN

Disclosed relates to a simplified method for resolving enantiomers by dissolving a racemic mixture having chiral carbon in α-position of nitrogen and an amino acid to prepare a diastereomeric salt, not using catalyses or enzymes, with enhancing the optical purity remarkably. Moreover, the present invention can prepare the enantiomers in large quantities without using expensive catalysts or without controlling the reaction conditions for the activity of enzymes applied.

Enantioselective synthesis of (R)-(+)- and (S)-(-)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation

Optically active tetrahydroisoquinoline alkaloids, (R)-(+)-higenamine (1R) and (S)-(-)-higenamine (1 S), and their optically active 1-naphthylmethyl analogues (2 and 3), were synthesized by enantioselective hydrogenation of the corresponding dihydroisoqui

METHOD FOR RESOLVING ENANTIOMERS FROM RACEMIC MIXTURE HAVING CHIRAL CARBON IN ALPHA POSITION OF NITROGEN

Disclosed relates to a simplified method for resolving enantiomers by dissolving a racemic mixture having chiral carbon in α-position of nitrogen and an amino acid to prepare a diastereomeric salt, not using catalyses or enzymes, with enhancing the optical purity remarkably. Moreover, the present invention can prepare the enantiomers in large quantities without using expensive catalysts or without controlling the reaction conditions for the activity of enzymes applied.

NOVEL ENANTIOMERS OF TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS

The disclosure concerns novel enantiomers of tetrahydroisoquinoline derivatives and their pharmaceutically acceptable salts, their preparations and pharmaceutical compositions. The enantiomers of tetrahydroisoquinoline derivatives are provided which are useful in stimulating heart rate and hypotensive activity, inhibitory activity against platelet aggregation, and suppressive against inducible NO synthase. The enantiomers of tetrahydroisoquinoline derivatives and their pharmaceutically acceptable salts are effective for treating congestive heart failure, hypertension, thrombosis, inflammation, septicemia, cardiac insufficiency, and disseminated intravascular coagulopathy.

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.