(2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS No.: 612820-02-7
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 612820-02-7.mol

Synonyms:(2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of (2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 1 articles about (2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl 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: 65.0%

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) + 3-bromo-1-phenyl-1-propenyl bromide (4392-24-9) → (2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (612820-02-7)

Guidance literature:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

3-bromo-1-phenyl-1-propenyl bromide; In tetrahydrofuran; at -78 ℃; for 1h;

Reference yield:

(2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (612820-02-7) → (2S,4R,5S)-5-Allyl-4-(3-phenyl-propyl)-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / hydrogen / Pd/C / methanol / 14 h / 20 °C

2: LiEt₃BH / tetrahydrofuran / -78 °C

3: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4: boron trifluoride etherate / toluene / -78 °C

5: 91 percent / trifluoroacetic acid / CH₂Cl₂ / 20 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; lithium triethylborohydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

Reference yield:

(2S,4R)-5-oxo-4-(3-phenylallyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (612820-02-7) → (2S,4R,5S)-4-(3-Phenyl-propyl)-5-((Z)-propenyl)-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / hydrogen / Pd/C / methanol / 14 h / 20 °C

2.1: LiEt₃BH / tetrahydrofuran / -78 °C

3.1: p-toluenesulfonic acid / methanol

4.1: CuBr*Me₂S / diethyl ether / -40 °C

4.2: boron trifluoride etherate / diethyl ether / -78 °C

4.3: diethyl ether / -78 - 0 °C

5.1: trifluoroacetic acid / CH₂Cl₂ / 20 °C

With copper(I) bromide dimethylsulfide complex; hydrogen; lithium triethylborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

3-bromo-1-phenyl-1-propenyl bromide

Downstream raw materials:

(2S,4R,5S)-1-acryloyl-5-allyl-4-(3-phenylpropyl)pyrrolidine-2-carboxylic acid methyl ester

(2S,4R,5S)-4-(3-phenylpropyl)-5-cis-propenylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,4R,5S)-1-but-3-enoyl-4-(3-phenylpropyl)-5-cis-propenylpyrrolidine-2-carboxylic acid methyl ester

(2S,4R,5S)-5-allyl-1-but-3-enoyl-4-(3-phenylpropyl)pyrrolidine-2-carboxylic acid methyl ester

Refernces