(±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid

Base Information

• Chemical Name: (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid
• CAS No.: 52635-97-9
• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.448

Synonyms:(±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid

Chemical Property of (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid

Chemical Property:

Purity/Quality:

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Technology Process of (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid

There total 17 articles about (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic 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: 75.0%

1-(2-tert-butoxycarbonylamino-phenyl)-8-(2-tert-butoxycarbonyl-ethyl)-8-ethyl-5,6,7,8-tetrahydro-indolizine-3-carboxylic acid methyl ester (281676-26-4) → (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid (52635-97-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja0003223

Reference yield:

3,3-diethyl-3,4,5,6-tetrahydropyridine (67625-92-7) → (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid (52635-97-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / dimethylformamide / 0.25 h / 80 °C

2: 51 percent / Ag₂CO₃ / toluene / 0.75 h / Heating

4: NaOMe

5: H₂ / Pd/C / 760.05 Torr

6: 83 percent / toluenesulfonic acid / toluene / 30 h / Heating

7: 54 mg

8: 76 percent / DMAP

9: OsO₄; NaIO₄

11: H₂ / Pd/C

12: 75 percent / TFA / CH₂Cl₂

With dmap; sodium periodate; osmium(VIII) oxide; o-toluenesulfonic acid; hydrogen; sodium methylate; silver carbonate; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Alkylation / 2: Cyclization / 3: Acylation / 4: Substitution / 5: Reduction / 6: Condensation / 8: Acylation / 9: Oxidation / 10: Substitution / 11: Catalytic hydrogenation / 12: acidolysis;

DOI:10.1021/ja0003223

Reference yield:

(E)-1-(3-bromoprop-1-en-1-yl)-2-nitrobenzene (111678-15-0) → (±)-3-(1-(2-aminophenyl)-8-ethyl-3-(methoxycarbonyl)-5,6,7,8-tetrahydroindolizin-8-yl)propanoic acid (52635-97-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / dimethylformamide / 0.25 h / 80 °C

2: 51 percent / Ag₂CO₃ / toluene / 0.75 h / Heating

4: NaOMe

5: H₂ / Pd/C / 760.05 Torr

6: 83 percent / toluenesulfonic acid / toluene / 30 h / Heating

7: 54 mg

8: 76 percent / DMAP

9: OsO₄; NaIO₄

11: H₂ / Pd/C

12: 75 percent / TFA / CH₂Cl₂

With dmap; sodium periodate; osmium(VIII) oxide; o-toluenesulfonic acid; hydrogen; sodium methylate; silver carbonate; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Alkylation / 2: Cyclization / 3: Acylation / 4: Substitution / 5: Reduction / 6: Condensation / 8: Acylation / 9: Oxidation / 10: Substitution / 11: Catalytic hydrogenation / 12: acidolysis;

DOI:10.1021/ja0003223

upstream raw materials:

1-(2-tert-butoxycarbonylamino-phenyl)-8-(2-tert-butoxycarbonyl-ethyl)-8-ethyl-5,6,7,8-tetrahydro-indolizine-3-carboxylic acid methyl ester

3,3-diethyl-3,4,5,6-tetrahydropyridine

(E)-1-(3-bromoprop-1-en-1-yl)-2-nitrobenzene

8,8-diethyl-1-(2-nitro-phenyl)-5,6,7,8-tetrahydro-indolizine

Downstream raw materials:

(±)-rhazinilam

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