methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate

Base Information

• Chemical Name: methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate
• CAS No.: 528607-67-2
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.449
• Mol file: 528607-67-2.mol

Synonyms:methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate

Chemical Property of methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate

There total 10 articles about methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate 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: 64.0%

2-anilineboronic acid pinacol ester (191171-55-8) + methyl (+/-)-8-ethyl-3-formyl-5,6,7,8-tetrahydro-1-iodoindolizin-8-propionate (528607-63-8) → methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate (528607-67-2)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; toluene; at 90 ℃; for 1.5h;

DOI:10.1039/b209992f

Reference yield:

4-(pyrrol-1-yl)butanoic acid (70686-51-0) → methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate (528607-67-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 87 percent / Et₃N; (2-pyridine N-oxide)disulfide; Bu₃P / 16 h / 18 °C

2.1: diethyl ether / 1 h / 18 °C

2.2: 95 percent / aq. KHSO₄ / diethyl ether / 0.1 h / -40 °C

3.1: 77 percent / NaH / 48 h / 18 °C

4.1: 83 percent / AlCl₃ / diethyl ether / 5 h / 18 °C

5.1: 75 percent / DIBAL-H / hexane / 0.16 h / -78 °C

6.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 91 percent / DMPU / 24 h / 18 °C

8.1: aq. KOH / methanol / 16 h / Heating

9.1: 72 percent / DCC; DMAP / CH₂Cl₂; methanol / 3 h / 18 °C

10.1: 78 percent / POCl₃ / diethyl ether / 3.5 h / 0 - 18 °C

11.1: 100 percent / I₂; silver trifluoroacetate / CHCl₃ / 4 h / 18 °C

12.1: 64 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / methanol; toluene / 1.5 h / 90 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; aluminium trichloride; tributylphosphine; (2-pyridine N-oxide)disulfide; iodine; silver trifluoroacetate; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triethylamine; dicyclohexyl-carbodiimide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; 3.1: Wadsworth-Emmons reaction / 4.1: Michael addition / 10.1: Vilsmeier-Haack formylation / 12.1: Suzuki-Miyuara cross-coupling;

DOI:10.1039/b209992f

Reference yield:

6-(1H-pyrrol-1-yl)hexan-6-one (292067-24-4) → methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate (528607-67-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / NaH / 48 h / 18 °C

2: 83 percent / AlCl₃ / diethyl ether / 5 h / 18 °C

3: 75 percent / DIBAL-H / hexane / 0.16 h / -78 °C

4: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: 91 percent / DMPU / 24 h / 18 °C

6: aq. KOH / methanol / 16 h / Heating

7: 72 percent / DCC; DMAP / CH₂Cl₂; methanol / 3 h / 18 °C

8: 78 percent / POCl₃ / diethyl ether / 3.5 h / 0 - 18 °C

9: 100 percent / I₂; silver trifluoroacetate / CHCl₃ / 4 h / 18 °C

10: 64 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / methanol; toluene / 1.5 h / 90 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; aluminium trichloride; iodine; silver trifluoroacetate; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triethylamine; dicyclohexyl-carbodiimide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; 1: Wadsworth-Emmons reaction / 2: Michael addition / 8: Vilsmeier-Haack formylation / 10: Suzuki-Miyuara cross-coupling;

DOI:10.1039/b209992f

upstream raw materials:

2-anilineboronic acid pinacol ester

methyl (+/-)-8-ethyl-3-formyl-5,6,7,8-tetrahydro-1-iodoindolizin-8-propionate

4-(pyrrol-1-yl)butanoic acid

6-(1H-pyrrol-1-yl)hexan-6-one