(2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Base Information

• Chemical Name: (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide
• CAS No.: 123724-30-1
• Molecular Formula: C₂₁H₂₄N₂O₂
• Molecular Weight: 336.434
• Mol file: 123724-30-1.mol

Synonyms:(2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Chemical Property of (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

There total 2 articles about (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide 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: 50.0%

(S)-1-phenyl-ethylamine (2627-86-3) + N-acetyl-trans-3-phenylproline (123807-03-4) → (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (123724-30-1) + (2S,3R)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (123724-28-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 3h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00288a045

Reference yield:

N-acetyl-3-phenylproline ethyl ester (179601-45-7) → (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (123724-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / 1. 1 M NaOEt, ethyl trifluoroacetate 2. H₂O / 1. EtOH, reflux, 2 h 2. room temp., 2.5 h

2: EDCI, HOBt*H₂O / dimethylformamide / 3 h / Ambient temperature

With ethyl trifluoroacetate,; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00288a045

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (123724-30-1) → (2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid (123724-32-3,210420-48-7,149252-59-5)

Guidance literature:

With hydrogenchloride; acetic acid; triethylamine; Yield given. Multistep reaction; 1. heating, 18 h 2. H₂O/dioxane, 4 + 18 h;

DOI:10.1021/jo00288a045

upstream raw materials:

(S)-1-phenyl-ethylamine

N-acetyl-trans-3-phenylproline

N-acetyl-3-phenylproline ethyl ester

Downstream raw materials:

(2S,3R)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid

(2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid