(2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 136092-34-7
• Molecular Formula: C₂₁H₂₉NO₃
• Molecular Weight: 343.466
• Mol file: 136092-34-7.mol

Synonyms:(2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester 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: 78.0%

(2R,5R)-2-Butyl-5-(2-oxo-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester (136092-33-6) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester (136092-34-7)

Guidance literature:

In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)92707-2

Reference yield:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester (136092-34-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 61 percent / diethyl ether; CH₂Cl₂ / -30 °C

3: Ni(acac)2 / CHCl₃

4: NaOMe

5: 76 percent / H₂, HCl / Raney Ni / methanol / 75005.9 Torr

6: LiAlH₄ / diethyl ether

8: PCC / CH₂Cl₂

9: 78 percent / tetrahydrofuran / Heating

With hydrogenchloride; bis(acetylacetonate)nickel(II); lithium aluminium tetrahydride; hydrogen; sodium methylate; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform;

DOI:10.1016/S0040-4039(00)92707-2

Reference yield:

(R)-2-Butyl-5-methoxy-3,4-dihydro-2H-pyrrole → (2R,5R)-2-Butyl-5-((E)-4-oxo-pent-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester (136092-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1: Ni(acac)2 / CHCl₃

2: NaOMe

3: 76 percent / H₂, HCl / Raney Ni / methanol / 75005.9 Torr

4: LiAlH₄ / diethyl ether

6: PCC / CH₂Cl₂

7: 78 percent / tetrahydrofuran / Heating

With hydrogenchloride; bis(acetylacetonate)nickel(II); lithium aluminium tetrahydride; hydrogen; sodium methylate; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform;

DOI:10.1016/S0040-4039(00)92707-2

upstream raw materials:

(2R,5R)-2-Butyl-5-(2-oxo-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

1-triphenylphosphoranylidene-2-propanone

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

2-((R)-5-Butyl-pyrrolidin-2-yl)-ethanol

Downstream raw materials:

(2R,5S)-(+)-2-n-butyl-5-(4-oxopentyl)pyrrolidine-1-carboxylic acid benzyl ester