(R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide
• CAS No.: 1245747-92-5
• Molecular Formula: C₁₈H₂₆N₂O₂
• Molecular Weight: 302.417
• Mol file: 1245747-92-5.mol

Synonyms:(R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide

Chemical Property of (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide

There total 4 articles about (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide 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: 84.0%

(3R,7aR)-7a-(3-methylbut-2-en-1-yl)-3-(trichloromethyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-1-one + 4-methoxy-benzylamine (2393-23-9) → (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide (1245747-92-5)

Guidance literature:

(3R,7aR)-7a-(3-methylbut-2-en-1-yl)-3-(trichloromethyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-1-one; 4-methoxy-benzylamine; at 80 ℃; for 6.5h; Inert atmosphere;

With sodium hydroxide; In ethanol; water; for 24h; Reflux; Inert atmosphere;

DOI:10.1039/c9cc00945k

Reference yield:

(3R,7aR)-3-tert-butyl-7a-(3-methylbut-2-enyl)-tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one (1138161-17-7) + 4-methoxy-benzylamine (2393-23-9) → (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide (1245747-92-5)

Guidance literature:

4-methoxy-benzylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(3R,7aR)-3-tert-butyl-7a-(3-methylbut-2-enyl)-tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

DOI:10.1016/j.tet.2010.04.093

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (R)-N-(4-methoxybenzyl)-2-(3-methylbut-2-en-1-yl)pyrrolidine-2-carboxamide (1245747-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chloroform / 6 h / Inert atmosphere; Reflux; Dean-Stark

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 - -40 °C / Inert atmosphere

3.1: neat (no solvent) / 6.5 h / 80 °C / Inert atmosphere

With lithium diisopropyl amide; In tetrahydrofuran; hexane; chloroform;

DOI:10.1039/c9cc00945k

upstream raw materials:

(3R,7aR)-3-tert-butyl-7a-(3-methylbut-2-enyl)-tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one

4-methoxy-benzylamine

L-proline

Downstream raw materials:

(R)-1-(3-(1H-indol-3-yl)-2-oxopropanoyl)-N-(4-methoxybenzyl)-2-(3-methyl-but-2-enyl)pyrrolidine-2-carboxamide

(8aR)-3-benzyl-3-hydroxy-2-(4-methoxybenzyl)-8a-(3-methylbut-2-enyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione