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

Base Information

• Chemical Name: (1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 171596-42-2
• Molecular Formula: C20H18N2O4
• Molecular Weight: 350.374
• UNII: ZZ2W6KC4KM
• Nikkaji Number: J3.236.689I
• Mol file: 171596-42-2.mol

Synonyms:171596-42-2;(1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;methyl (1S,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate;ZZ2W6KC4KM;SCHEMBL3847739;LIPVUDSNGRJSQE-QAPCUYQASA-;NSC809797;NSC-809797;CS-0166262;J-010740;(1S,3R)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate? (Tadalafil Impurity;1H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-, methyl ester, (1S,3R)-;InChI=1/C20H18N2O4/c1-24-20(23)15-9-13-12-4-2-3-5-14(12)21-19(13)18(22-15)11-6-7-16-17(8-11)26-10-25-16/h2-8,15,18,21-22H,9-10H2,1H3/t15-,18+/m1/s1;methyl (1S,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3, 4-b]indole-3-carboxylate

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

Chemical Property:

• 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.: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (S
• 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

(1S,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: An intermediate in the synthesis of thephosphodiesterase 5 inhibitor Tadalafil (T004500). (1S,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.

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

There total 21 articles about (1S,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: 98.0%

(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 (1453864-08-8) → (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)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In acetonitrile; at 60 ℃; for 8h; under 798.054 - 836.056 Torr;

DOI:10.1016/j.tetasy.2013.06.006

Reference yield: 95.0%

(S)-1-benzo[1,3]dioxol-5-yl-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline-(R)-3-carboxylic acid methyl ester (497182-99-7) → (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)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In acetonitrile; at 60 ℃; for 8h; under 798.054 - 836.056 Torr;

DOI:10.1016/j.tetasy.2013.06.006

Reference yield: 82.0%

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) + (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)

Guidance literature:

In isopropyl alcohol; for 24h; Reflux;

DOI:10.1021/acschemneuro.7b00345

upstream raw materials:

piperonal

D-Tryptophan methyl ester

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

methanol

Downstream raw materials:

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

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

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

(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

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