(2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 214334-47-1
• Molecular Formula: C₂₂H₃₃NO₃
• Molecular Weight: 359.509
• Mol file: 214334-47-1.mol

Synonyms:(2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 9 articles about (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-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: 89.0%

(2R,5S)-2-Heptyl-5-(3-hydroxy-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (214334-46-0) → (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (214334-47-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; for 0.75h;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1955::AID-EJOC1955>3.0.CO;2-U

Reference yield:

(S)-(1-tert-butoxycarbonyl-5-oxopyrrolidin-2-yl)-methyl-4-methylbenzenesulfonate (135697-21-1) → (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (214334-47-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 10.1 g / LiEt₃BH / CH₂Cl₂ / 4 h / -78 °C

2: 43 percent / CHCl₃ / 24 h / Heating

3: TiCl₄ / CH₂Cl₂ / -78 - 20 °C

4: 100 percent / KOH / dioxane / 64 h / Heating

5: 87 percent / Na₂CO₃ / CH₂Cl₂ / 20 °C

6: 98 percent / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

7: 79 percent / CuI / hexane; diethyl ether / -20 °C

8: 1.) BH₃*(CH₃)2S; 2.) NaOH, H₂O₂ / 1.) Et₂O, THF, r.t., 4 h; 2.) H₂O, reflux, 1 h

9: 89 percent / (COCl)2, NEt₃, DMSO / CH₂Cl₂ / 0.75 h / -60 °C

With potassium hydroxide; sodium hydroxide; copper(l) iodide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; titanium tetrachloride; lithium triethylborohydride; sodium carbonate; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; chloroform;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1955::AID-EJOC1955>3.0.CO;2-U

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2R,5S)-2-Heptyl-5-(3-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (214334-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / Na₂CO₃ / CH₂Cl₂ / 20 °C

2: 98 percent / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

3: 79 percent / CuI / hexane; diethyl ether / -20 °C

4: 1.) BH₃*(CH₃)2S; 2.) NaOH, H₂O₂ / 1.) Et₂O, THF, r.t., 4 h; 2.) H₂O, reflux, 1 h

5: 89 percent / (COCl)2, NEt₃, DMSO / CH₂Cl₂ / 0.75 h / -60 °C

With sodium hydroxide; copper(l) iodide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium carbonate; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1955::AID-EJOC1955>3.0.CO;2-U

upstream raw materials:

(2R,5S)-2-Heptyl-5-(3-hydroxy-propyl)-pyrrolidine-1-carboxylic acid benzyl ester

(S)-(1-tert-butoxycarbonyl-5-oxopyrrolidin-2-yl)-methyl-4-methylbenzenesulfonate

benzyl chloroformate

(5R,7aS)-5-Ethoxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

Downstream raw materials:

(2R,5S)-2-Heptyl-5-(3-hydroxy-butyl)-pyrrolidine-1-carboxylic acid benzyl ester

(2R,5S)-2-Heptyl-5-(3-oxo-butyl)-pyrrolidine-1-carboxylic acid benzyl ester