(1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

Base Information

• Chemical Name: (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 171596-41-1
• Molecular Formula: C20H18N2O4
• Molecular Weight: 350.374
• DSSTox Substance ID: DTXSID301117245
• Nikkaji Number: J2.568.853H
• Mol file: 171596-41-1.mol

Synonyms:171596-41-1;(1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1R,3R)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate;methyl (1r,3r)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-3-carboxylate;METHYL (1R,3R)-1-(2H-1,3-BENZODIOXOL-5-YL)-1H,2H,3H,4H,9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE;(1R,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;SCHEMBL1420216;DTXSID301117245;AMY40290;NSC809798;AKOS015965250;NSC-809798;AC-20402;AS-82503;A881919;J-010739;J-010741;(1R)-1beta-(1,3-Benzodioxole-5-yl)-1,2,3,4-tetrahydro-beta-carboline-3beta-carboxylic acid methyl ester;(1R, 3R)-Methyl-1,2,3,4-tetrahydro-1(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1R,3R)-Methyl 1,2,3,4-Tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1R,3R)-Methyl-1,2,3,4-tetrahydro-1(3,4-methylenedioxyphenyl)-9H-pyrido [3,4-b]indole-3-carboxylate;(1r,3r)-methyl1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9h-pyrido[3,4-b]indole-3-carboxylate;methyl (1R,3R)-1-(1,3-b enzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property of (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 83-85°C
• Boiling Point: 531.0±50.0 °C(Predicted)
• PKA: 16.87±0.60(Predicted)
• PSA: 72.58000
• Density: 1.359±0.06 g/cm3(Predicted)
• LogP: 3.00210
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 350.12665706
• Heavy Atom Count: 26
• Complexity: 544

Purity/Quality:

98%+ ^*data from raw suppliers

(1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2=C(C(N1)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25
• Isomeric SMILES: COC(=O)[C@H]1CC2=C([C@H](N1)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25
• Uses: (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate can be used as an intermediate in the synthesis of Tadafil, which is used for the treatment of erectile dysfunction. An intermediate and impurity in the synthesis of Tadafil. An intermediate and impurity in the synthesis of Tadalafil (T004500).

Technology Process of (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

There total 23 articles about (1R,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.2%

piperonal (120-57-0,30024-74-9) + D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1) → (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1)

Guidance literature:

With hydrogenchloride; In water; toluene; for 15h; Concentration; Solvent; Reflux; Large scale;

Reference yield: 94.2%

piperonal (120-57-0,30024-74-9) + (R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) → (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1)

Guidance literature:

In acetonitrile; at 75 - 85 ℃; for 16h; stereoselective reaction;

Reference yield: 92.0%

(1S,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester (171596-42-2) → (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1)

Guidance literature:

(1S,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester; With hydrogenchloride; In water; ethyl acetate; at 20 ℃;

In nitromethane; for 5h; Reflux;

With potassium carbonate; In water; ethyl acetate;

DOI:10.1016/j.tetasy.2009.07.048

upstream raw materials:

(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

piperonal

D-Tryptophan methyl ester

(R)-(+)-tryptophan methyl ester hydrochloride

Downstream raw materials:

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

C₃₇H₃₉N₃O₉

C₄₁H₃₈N₄O₉

(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-((R)-1-(4-dimethylaminobenzyl)pyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Refernces

• 1、 -. "NOVEL DUAL MODE OF ACTION SOLUBLE GUANYLATE CYCLASE ACTIVATORS AND PHOSPHODIESTERASE INHIBITORS AND USES THEREOF". Page/Page column 89. . Retrieved 2021/12/28.
• 2、 -. "Preparation method of tadalafil and intermediate of tadalafil". Paragraph 0035-0061. . Retrieved 2019/11/20.