(1R,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: (1R,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.: 171596-44-4
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350.374
• DSSTox Substance ID: DTXSID001117741
• ChEMBL ID: CHEMBL4632957
• Mol file: 171596-44-4.mol

Synonyms:171596-44-4;methyl (1R,3S)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-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;(1R,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;Tadalafil Impurity 7;CHEMBL4632957;LIPVUDSNGRJSQE-MAUKXSAKSA-N;DTXSID001117741;(1R, 3S) Methyl ester Tadalafil Impurity;(1R, 3S) methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3carboxylate

Chemical Property of (1R,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: 154 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 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:

97% ^*data from raw suppliers

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

Technology Process of (1R,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 7 articles about (1R,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: 47.0%

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) → (1R,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-44-4) + (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-43-3)

Guidance literature:

In ethanol; for 24h; Reflux;

DOI:10.1021/acschemneuro.7b00345

Reference yield: 42.0%

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) + (1R,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-44-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 4 ℃;

Reference yield: 36.0%

piperonal (120-57-0,30024-74-9) + L-tryptophan methyl ester (4299-70-1) → (1R,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-44-4) + (1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (171596-43-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jm0300577

upstream raw materials:

piperonal

L-tryptophan methyl ester

(S)-tryptophan methyl ester hydrochloride

D-Tryptophan methyl ester

Downstream raw materials:

(1R,3S)-1-benzo[1,3]dioxol-5-yl-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

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

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