2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole

Base Information

• Chemical Name: 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole
• CAS No.: 95305-17-2
• Molecular Formula: C₄₀H₅₅N₃O₆S
• Molecular Weight: 705.959
• Mol file: 95305-17-2.mol

Synonyms:

Chemical Property of 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole

There total 10 articles about 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole 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: 97.0%

5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-4,4-dimethylpyrrolidin-2-thione (95305-10-5) + tert-Butyl 5-benzyloxycarbonyl(bromo)methyl-4-ethyl-3-methylpyrrole-2-carboxylate (95305-16-1) → 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole (95305-17-2,95305-27-4)

Guidance literature:

With potassium tert-butylate; In tetrachloromethane; tert-butyl alcohol; for 1.5h;

DOI:10.1039/P19840002733

Reference yield:

Methyl 3,3-dimethylacrylate (924-50-5) → 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole (95305-17-2,95305-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / tetrabutylammonium fluoride, 3A molecular sieve / dimethylformamide / 4 h / 50 °C

2: 69 percent / zinc dust / acetic acid / 1.5 h / Ambient temperature

3: titanium(II) chloride / 0.33 h

4: 54 percent / phosphorus pentasulphide, pyridine / acetonitrile / 1.) 15 min, 2.) 20 deg C, 62 h

5: 97 percent / potassium t-butoxide / 2-methyl-propan-2-ol; CCl₄ / 1.5 h

With pyridine; diphosphorus pentasulfide; 3 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; titanium chloride; zinc; In tetrachloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1039/P19840002733

Reference yield:

5-tert-Butoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic Acid (31897-11-7) → 2--5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-3,4-dihydro-4,4-dimethylpyrrole (95305-17-2,95305-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride, DMF / CH₂Cl₂ / 0.83 h / Heating

2: diethyl ether / 1.) 0 deg C, 3 h, 2.) 20 deg C, 16 h

3: triethylamine / phenylmethanol / 1.5 h / 80 °C

4: N-bromosuccinimide / CCl₄ / 0.25 h / Heating; Irradiation

5: 97 percent / potassium t-butoxide / 2-methyl-propan-2-ol; CCl₄ / 1.5 h

With N-Bromosuccinimide; thionyl chloride; potassium tert-butylate; triethylamine; N,N-dimethyl-formamide; In tetrachloromethane; diethyl ether; dichloromethane; benzyl alcohol; tert-butyl alcohol;

DOI:10.1039/P19840002733

upstream raw materials:

5-(3-ethyl-4-methyl-5-t-butoxycarbonylpyrrol-2-ylmethyl)-4,4-dimethylpyrrolidin-2-thione

tert-Butyl 5-benzyloxycarbonyl(bromo)methyl-4-ethyl-3-methylpyrrole-2-carboxylate

Methyl 3,3-dimethylacrylate

5-tert-Butoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic Acid

Downstream raw materials:

di-t-butyl 5-benzyloxycarbonyl-3,12-diethyl-2,8,8,13-tetramethyl-7,8,9,10,16,17-hexahydrotripyrrin-1,14-dicarboxylate