1,2-Pyrrolidinedicarboxylic acid, 3-[2-(acetyloxy)ethyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,3R,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(acetyloxy)ethyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,3R,4R)-
• CAS No.: 873326-70-6
• Molecular Formula: C18H23NO7
• Molecular Weight: 365.383
• Mol file: 873326-70-6.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(acetyloxy)ethyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,3R,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(acetyloxy)ethyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,3R,4R)-

There total 4 articles about 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(acetyloxy)ethyl]-4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,3R,4R)- 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,3R,4R)-methyl 4-hydroxy-3-(2-hydroxyethyl)-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate (873326-65-9) → (2S,3R,4R)-1-benzyl 2-methyl 3-(2-acetoxyethyl)-4-hydroxypyrrolidine-1,2-dicarboxylate (873326-70-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / 3800 Torr

2: 574 mg / triethylamine / H₂O; dioxane / 24 h / 20 °C

3: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,3,5-trimethyl-pyridine; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo051508t

Reference yield:

(2S)-methyl 3-(2-methoxy-2-oxoethyl)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate → (2S,3R,4R)-1-benzyl 2-methyl 3-(2-acetoxyethyl)-4-hydroxypyrrolidine-1,2-dicarboxylate (873326-70-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

1.2: 70 percent / NaBH₄ / ethanol / 2 h / 0 °C

2.1: acetic acid; H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / 3800 Torr

3.1: 574 mg / triethylamine / H₂O; dioxane / 24 h / 20 °C

4.1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,3,5-trimethyl-pyridine; hydrogen; L-Selectride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo051508t

Reference yield:

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-76-8) → (2S,3R,4R)-1-benzyl 2-methyl 3-(2-acetoxyethyl)-4-hydroxypyrrolidine-1,2-dicarboxylate (873326-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium; HMPA / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 80 percent / sodium iodide / tetrahydrofuran / 1 h / -55 - -40 °C

2.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

2.2: 70 percent / NaBH₄ / ethanol / 2 h / 0 °C

3.1: acetic acid; H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / 3800 Torr

4.1: 574 mg / triethylamine / H₂O; dioxane / 24 h / 20 °C

5.1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen; L-Selectride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo051508t

upstream raw materials:

(2S,3R,4R)-methyl 4-hydroxy-3-(2-hydroxyethyl)-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(2S,3R,4R)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid