Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate

Base Information

• Chemical Name: Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate
• CAS No.: 145696-31-7
• Molecular Formula: C₂₈H₃₄N₂O₄
• Molecular Weight: 462.589

Synonyms:Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate

Chemical Property of Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate

Chemical Property:

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Technology Process of Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate

There total 16 articles about Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-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: 73.0%

Benzyl 6-Hydroxy-3-methylcyclopentapyrrole-2-carboxylate (145696-30-6) + tert-butyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate (75488-15-2) → Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate (145696-31-7)

Guidance literature:

With toluene-4-sulfonic acid; In acetic acid; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85734-3

Reference yield:

4-ethyl-3,5-dimethyl-pyrrole-2-carboxylic acid tert-butyl ester (31896-92-1) → Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate (145696-31-7)

Guidance literature:

Multi-step reaction with 5 steps

1: SO₂Cl₂, K₂CO₃ / diethyl ether / 24 h / Ambient temperature

2: aq. NaHCO₃ / dioxane / 0.67 h / 70 °C

3: 80 percent / NaHCO₃, I₂, KI / methanol; H₂O / 1 h / 60 - 65 °C

4: 95 percent / CH₃CO₂Na, H₂ / PtO₂ / ethanol / 24 h / 1551.4 Torr / Ambient temperature

5: 73 percent / p-TsOH / acetic acid / 1.5 h / Ambient temperature

With sulfuryl dichloride; hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; potassium iodide; platinum(IV) oxide; In 1,4-dioxane; methanol; diethyl ether; ethanol; water; acetic acid;

DOI:10.1016/S0040-4020(01)85734-3

Reference yield:

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate (20303-31-5) → Benzyl 6-(5-tert-Butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylcyclopentapyrrole-2-carboxylate (145696-31-7)

Guidance literature:

Multi-step reaction with 8 steps

1: SO₂Cl₂ / diethyl ether / 48 h / Ambient temperature

2: CH₃CO₂Na*3H₂O / dioxane; H₂O / 1) 70 deg C, 1.5 h, 2) rt, overnight

3: 95 percent / NaHCO₃, I₂, KI / methanol; H₂O / 1 h / 60 - 65 °C

4: 92 percent / CH₃CO₂Na, H₂ / PtO₂ / ethanol / 24 h / 1551.4 Torr / Ambient temperature

5: 91 percent / aq. HCl / acetone / 3 h / Heating

6: 1a) KOH, 1b) oxalyl chloride / 2) SnCl₄ / 1a) CH₃OH, 1b) toluene, rt, 3 h, 2) rt, 1 h

7: 82 percent / NaBH₄ / 1) ethanol, rt, 10 min, 2) water, heating

8: 73 percent / p-TsOH / acetic acid / 1.5 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; sulfuryl dichloride; oxalyl dichloride; hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; potassium iodide; platinum(IV) oxide; tin(IV) chloride; In 1,4-dioxane; methanol; diethyl ether; ethanol; water; acetic acid; acetone;

DOI:10.1016/S0040-4020(01)85734-3

upstream raw materials:

Benzyl 6-Hydroxy-3-methylcyclopentapyrrole-2-carboxylate

tert-butyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate

benzyl 6-acetoxy-3-methylcyclopentapyrrole-2-carboxylate

cyclopentanone

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