54417-52-6

Basic information

• Product Name: (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride
• Synonyms: (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride
• CAS NO: 54417-52-6
• Molecular Weight: 379.884
• Mol File: 54417-52-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride(54417-52-6)
• EPA Substance Registry System: (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride(54417-52-6)

Safety Data

• Hazardous Substances Data: 54417-52-6(Hazardous Substances Data)

Upstream product

• 6957-27-3 3,4-dihydropapaverine 
• 74-88-4 methyl iodide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 

Downstream Products

• 1354039-86-3 (R)-2-[(S)-(1-3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-isopropyl-2-phenylacetamide 

Relevant articles and documents

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

1,2,3,4-tetrahydroisoquinoline derivative and its use as orexin receptor antagonist

The invention relates to the compound (R)-2-[(S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-isopropyl-2-phenyl-acetamide; and to its use as active ingredient in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compound, pharmaceutical compositions containing the compound and methods of treatment comprising administration of said compound to a human being.

A Novel Asymmetric Reduction of Imines with Chiral Sodium Triacyloxyborohydrides

There has been described a novel and convenient synthesis of optically active alkaloids by the asymmetric reduction of cyclic imines using the chiral sodium triacyloxyborohydrides, easily prepared from the reaction of NaBH4 and N-acyl L-prolines.