153874-43-2

Basic information

• Product Name: benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate
• Synonyms: benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate
• CAS NO: 153874-43-2
• Molecular Weight: 306.364
• Mol File: 153874-43-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate(153874-43-2)
• EPA Substance Registry System: benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate(153874-43-2)

Safety Data

• Hazardous Substances Data: 153874-43-2(Hazardous Substances Data)

Upstream product

• 16502-01-5 tetrahydrobetacarboline 
• 501-53-1 benzyl chloroformate 
• 190788-59-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 286961-24-8 benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate 
• 102991-38-8 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 61-54-1 tryptamine 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 615-36-1 2-bromoaniline 
• 1579291-50-1 benzyl 4-(2-azidophenyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 1579291-74-9 2-(2-azidophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 

Downstream Products

• 170864-80-9 2-benzyloxycarbonyl-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole 
• 311761-23-6 2-benzyloxycarbonyl-9-{[4-(fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole 
• 908287-35-4 (±)-benzyl 2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate 
• 16502-01-5 tetrahydrobetacarboline 
• 1356026-83-9 C₁₉H₁₈N₂O₃ 
• 1189555-55-2 [4-[2-(9-benzenesulfonyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(3-fluorophenyl)cyclohexyl]dimethylamine 

Relevant articles and documents

CuII/TEMPO-Catalyzed Enantioselective C(sp3)–H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.

Hydroxymethylcyclohexylamines

The invention relates to compounds which have an affinity for the μ opioid receptor and the ORL1 receptor, processes for the preparation thereof, medicaments containing these compounds and the use of these compounds for the preparation of medicaments.