(1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester

Base Information

• Chemical Name: (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester
• CAS No.: 171596-43-3
• Molecular Formula: C20H18N2O4
• Molecular Weight: 350.374
• DSSTox Substance ID: DTXSID001117222
• Nikkaji Number: J2.772.718B
• ChEMBL ID: CHEMBL4649538
• Mol file: 171596-43-3.mol

Synonyms:171596-43-3;(1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;methyl (1S,3S)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate;(1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl;(1S,3S)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate;Tadalafil Impurity 3;SCHEMBL3866508;CHEMBL4649538;LIPVUDSNGRJSQE-YJBOKZPZSA-N;DTXSID001117222;(1S-cis) Methyl ester Tadalafil Impurity;CS-0166256;(1S)-1alpha-(1,3-Benzodioxole-5-yl)-1,2,3,4-tetrahydro-beta-carboline-3alpha-carboxylic acid methyl ester;(1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate? (Tadalafil Impurity;(1S-cis)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;1H-Pyrido[3,4-b]indole-3-carboxylicacid, 1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-methylester,(1R,3R)-;cis-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester

Chemical Property of (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester

Chemical Property:

• Melting Point: 187-189 °C(Solv: methanol (67-56-1))
• 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), DMSO (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

(1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylicAcidMethylEster ^*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: (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester is used in the preparation of pyrazinopyridoindole derivatives for their PDE5 inhibitory activity.

Technology Process of (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester

There total 10 articles about (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester 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: 95.0%

piperonal (120-57-0,30024-74-9) + (S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-43-3)

Guidance literature:

piperonal; (S)-tryptophan methyl ester hydrochloride; In nitromethane; Reflux;

With potassium carbonate; In water; ethyl acetate; stereoselective reaction;

DOI:10.1016/j.tetasy.2009.07.048

Reference yield: 62.0%

(1S)-2-benzyl 3-methyl 1-(benzo[d][1,3]dioxol-5-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,3-dicarboxylate → (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) + (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-43-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃;

DOI:10.1016/j.tetasy.2009.07.048

Reference yield: 62.0%

methyl (S,E)-2-((benzo[d][1,3]dioxol-5-ylmethylene)amino)-3-(2-bromo-1H-indol-3-yl)propanoate → 1-(3,4-methylenedioxy-phenyl)-β-carboline-3-carboxylic acid methyl ester (321862-32-2) + (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-43-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 5h; Inert atmosphere; Heating;

DOI:10.1002/adsc.202100506

upstream raw materials:

piperonal

L-tryptophan methyl ester

ethanol

L-Tryptophan

Downstream raw materials:

(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

(1S,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester

(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

methyl (1S,3S)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

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