1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate
• CAS No.: 851390-89-1
• Molecular Formula: C₁₃H₂₂ClNO₂
• Molecular Weight: 259.776
• Mol file: 851390-89-1.mol

Synonyms:1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate

Chemical Property of 1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate

There total 1 articles about 1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-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:

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) + 4-chloro-2-iodo-but-1-ene (335428-13-2) → 1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate (851390-89-1) + 1,1-dimethylethyl (2S)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate

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 0.5h;

4-chloro-2-iodo-but-1-ene; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2005.01.094

Reference yield: 92.0%

1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate (851390-89-1) → (R)-hexahydro-1-methylene-1H-pyrrolizine (851390-88-0)

Guidance literature:

1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate; With chloro-trimethyl-silane; In methanol; at 25 ℃; for 12h;

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2005.01.094

Reference yield:

1,1-dimethylethyl (2R)-2-(3-chloro-1-methylene-propyl)-1-pyrrolidinecarboxylate (851390-89-1) → (+)-pseudoheliotridane (178035-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilylchloride / methanol / 12 h / 25 °C

1.2: 92 percent / NaHCO₃ / tetrahydrofuran; H₂O

2.1: H₂ / Pd/C / CH₂Cl₂ / 20 °C

With chloro-trimethyl-silane; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.01.094

upstream raw materials:

tert-butyl pyrrolidine-1-carboxylate

4-chloro-2-iodo-but-1-ene

Downstream raw materials:

(R)-hexahydro-1-methylene-1H-pyrrolizine

(+)-pseudoheliotridane