171596-42-2

Basic information

• Product Name: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• Synonyms: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1S,3R)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;Tadalafil Impuirty Ⅵ
• CAS NO: 171596-42-2
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350
• Product Categories: Chiral Reagents
• Mol File: 171596-42-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 531.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.359±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (S
• PKA: 16.87±0.60(Predicted)
• CAS DataBase Reference: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate(171596-42-2)
• EPA Substance Registry System: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate(171596-42-2)

Safety Data

• Hazardous Substances Data: 171596-42-2(Hazardous Substances Data)

Usage

Description

(1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate is a complex organic compound characterized by its light yellow powder form. It is a specific stereoisomer with the 1S,3R configuration, which plays a crucial role in its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate is used as an intermediate in the synthesis of Tadalafil (T004500) for the treatment of erectile dysfunction. Tadalafil is a phosphodiesterase 5 inhibitor that helps improve blood flow to the penis, allowing for a stronger and more sustained erection in response to sexual stimulation.
As an intermediate in the synthesis of Tadalafil, this compound is essential for the development of medications that address erectile dysfunction, a common condition affecting many men worldwide. Its role in the pharmaceutical industry highlights the importance of its chemical properties and the potential for further research and development in this area.

Upstream product

• 120-57-0 piperonal 
• 4299-70-1 D-Tryptophan methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 67-56-1 methanol 
• 474668-76-3 (1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid hydrochloride 
• 153-94-6 D-tryptophan 
• 4299-70-1 L-tryptophan methyl ester 
• 1453863-96-1 (1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 171596-43-3 (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 1453863-95-0 (1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-1-yl-methyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 1453864-08-8 (1S,3R)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-1-yl-methyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 497182-99-7 (S)-1-benzo[1,3]dioxol-5-yl-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline-(R)-3-carboxylic acid methyl ester 
• 17680-04-5 (3,4-methylenedioxy)phenylmagnesium bromide 
• 171752-68-4 (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride 

Downstream Products

• 497182-99-7 (S)-1-benzo[1,3]dioxol-5-yl-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline-(R)-3-carboxylic acid methyl ester 
• 531500-48-8 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione 
• 531500-48-8 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione 
• 629652-72-8 (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1′,2’:1,6]-pyrido[3,4-b]indole-1,4-dione 
• 171596-28-4 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione 
• 171596-41-1 (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate 
• 1018814-78-2 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-((R)-1-benzylpyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione 
• 171489-59-1 methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate 

Relevant articles and documents

Preparation method of tadalafil intermediate impurity

A preparation method of a tadalafil intermediate impurity comprises the following steps: firstly, fully dissolving raw materials in an isomerization solvent, sequentially carrying out a heating reflux reaction and vacuum concentration to obtain a residue I, adding an alkaline solution and an extraction solvent into the residue I, sequentially carrying out room temperature stirring and standing, then taking an organic phase, and carrying out vacuum evaporation to dryness to obtain a residue II; and adding a resolving solvent into the residue II, sequentially carrying out heating reflux reaction, natural stirring crystallization and filtration to obtain filtrate and a filter cake, and finally drying the filter cake to obtain an intermediate impurity, wherein the temperature of natural stirring crystallization is 30-60 DEG C. According to the preparation method, the principle that the intermediates and the reaction byproducts have different solubilities in the resolving solvents at different temperatures is utilized, the intermediates and the reaction byproducts are resolved, the preparation efficiency is high, the cost is low, and the purity of the prepared intermediates is high.

3,4-methylenedioxyphenyl substituted tetrahydro-beta-carboline piperazine dione derivative and uses thereof

The present invention relates to a 3,4-methylenedioxyphenyl substituted tetrahydro-beta-carboline piperazine dione derivative and uses thereof, and specifically discloses a compound represented by a formula I, or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein each group is defined in the specification. According to the present invention, the compound has dual inhibitory activity on acetylcholinesterase and phosphodiesterase 5, and has good blood-brain barrier permeability, such that the compound can be used for preparing drugs for treatment and/or prevention ofAlzheimer's diseases. The formula I is defined in the specification.

Preparation method of tadalafil

The invention discloses a preparation method of tadalafil, starting material D-Tryptophan methyl ester hydrochloride is reacted with oxalyl chloride to obtain an intermediate III, and the final product tadalafil (I) is obtained through cyclization, Grignard reaction, asymmetric reduction, substitution and condensation reaction. The use of national control chemical piperonal is avoided, an intermediate VI can be highly-selectively obtained by the asymmetric reduction, and the method has the advantages of simple postprocessing, short synthesis steps and high product total yield, and is suitable for industrialized production.