benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate

Base Information

• Chemical Name: benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate
• CAS No.: 474417-76-0
• Molecular Formula: C₁₈H₂₂F₃NO₅
• Molecular Weight: 389.372
• Mol file: 474417-76-0.mol

Synonyms:benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate

Chemical Property of benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate

There total 6 articles about benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate 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:

(2S,4S)-4-Trifluoromethyl-4-trimethylsilanyloxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester → benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate (474417-76-0)

Guidance literature:

With tetrabutyl ammonium fluoride; ammonium chloride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo0257400

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate (474417-76-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aqueous NaOH / tetrahydrofuran; H₂O / 20 °C

2: 6.17 g / Et₃N / tetrahydrofuran / 0 - 20 °C

3: 84 percent / chromium trioxide; pyridine / CH₂Cl₂ / 4 h / 20 °C

4: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

5: 2.97 g / aqueous NH₄Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With pyridine; chromium(VI) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; ammonium chloride; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo0257400

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate (474417-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 6.17 g / Et₃N / tetrahydrofuran / 0 - 20 °C

2: 84 percent / chromium trioxide; pyridine / CH₂Cl₂ / 4 h / 20 °C

3: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

4: 2.97 g / aqueous NH₄Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With pyridine; chromium(VI) oxide; tetrabutyl ammonium fluoride; ammonium chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0257400

upstream raw materials:

di-tert-butyl dicarbonate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4S)-1-[(tert-butoxy)carbonyl]-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid

Refernces