1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate
• CAS No.: 350022-50-3
• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.341
• Mol file: 350022-50-3.mol

Synonyms:1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate

Chemical Property of 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate

There total 1 articles about 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate 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:

ethyl (Z)-3-iodopropenoate (31930-36-6) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → 1,1-dimethylethyl 2(S)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate (356788-89-1) + 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate (350022-50-3)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; at -78 ℃; for 1h;

With lithium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

ethyl (Z)-3-iodopropenoate; In tetrahydrofuran; diethyl ether; at -78 - 25 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1021/jo035845i

Reference yield:

1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate (350022-50-3) → 5,6,7,7a-Tetrahydro-3H-pyrrolizin-3-on (113727-94-9,766516-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / chlorotrimethylsilane / methanol / 20 °C

2: 96 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

With chloro-trimethyl-silane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol;

DOI:10.1021/jo049460r

Reference yield:

1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate (350022-50-3) → pyrrolam A (126424-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / chlorotrimethylsilane / methanol / 20 °C

2: 91 percent / NaHCO₃ / CH₂Cl₂; H₂O

With chloro-trimethyl-silane; sodium hydrogencarbonate; In methanol; dichloromethane; water;

DOI:10.1021/jo049460r

upstream raw materials:

ethyl (Z)-3-iodopropenoate

tert-butyl pyrrolidine-1-carboxylate

Downstream raw materials:

pyrrolam A

5,6,7,7a-Tetrahydro-3H-pyrrolizin-3-on

1,2,5,6-tetrahydro-3H-pyrrolizin-3-one