2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

Base Information

• Chemical Name: 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid
• CAS No.: 229008-37-1
• Molecular Formula: C₂₂H₂₃NO₂
• Molecular Weight: 333.43

Synonyms:2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

Chemical Property of 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

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Technology Process of 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

There total 12 articles about 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid 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: 100.0%

3-(4-pyrrolidin-1-yl-phenyl)-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester (229008-36-0) → 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (229008-37-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1021/jm9906264

Reference yield:

4-(1-pyrrolidinyl)phenyl borate + methyl 2-bromo-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (229007-63-0) → 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (229008-37-1)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine)palladium ⁽⁰⁾; In tetrahydrofuran; methanol; sodium hydroxide; ethanol; toluene;

Reference yield:

ethyl glutaroyl chloride (5205-39-0) → 2-(4-(1-pyrrolidinyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (229008-37-1)

Guidance literature:

Multi-step reaction with 10 steps

1: AlCl₃ / 3.5 h / 20 °C

2: 2 N aq. NaOH / methanol / 1.5 h / Heating

3: 73 percent / triethylsilane; TFA / 48 h / 55 °C

4: 67 percent / polyphosphoric acid / 12 h / 100 °C

5: 64 percent / NaOMe / 8 h / Heating

6: 86 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -10 °C

7: Et₃N / CH₂Cl₂ / 20 °C

8: 74 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

9: 77 percent / tetrakis(triphenylphosphine)palladium; 2 M aq. K₂CO₃ / ethanol; toluene / Heating

10: 100 percent / 1 N aq. NaOH / methanol; tetrahydrofuran / 20 °C

With triethylsilane; sodium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; PPA; sodium methylate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: Friedel-Crafts reaction / 2: Hydrolysis / 3: Reduction / 4: intramolecular Friedel-Crafts reaction / 5: methoxycarbonylation / 6: Reduction / 7: mesylation / 8: Elimination / 9: Suzuki coupling / 10: Hydrolysis;

DOI:10.1021/jm9906264

upstream raw materials:

3-(4-pyrrolidin-1-yl-phenyl)-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester

ethyl glutaroyl chloride

bromobenzene

4-bromo-δ-oxobenzenepentanoic acid

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