(S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 212387-69-4
• Molecular Formula: C₂₈H₃₀N₂O₈
• Molecular Weight: 522.555
• Mol file: 212387-69-4.mol

Synonyms:(S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 8 articles about (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl 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: 75.0%

phthalimide (136918-14-4,85-41-6) + (R)-2-tert-Butoxycarbonylmethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (212387-68-3) → (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (212387-69-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; 1.) -23 deg C, 2.) r.t.;

DOI:10.1039/cc9960002155

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (212387-69-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / 1 M aq. Na₂CO₃ / dioxane / Ambient temperature

2: 100 percent / Et₃N / tetrahydrofuran / 21 h

3: 1.) LDA / 1.) THF, hexane, -70 deg C, 30 min, 2.) THF, hexane, RT, overnight

4: 10percent methanol. citric acid / 3 h / Ambient temperature

5: 70 percent / PPh₃, DEAD / tetrahydrofuran / -25 - 20 °C

With sodium carbonate; triethylamine; triphenylphosphine; citric acid; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/ja980444j

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → (S)-2-tert-Butoxycarbonylmethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (212387-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / Et₃N / tetrahydrofuran / 21 h

2: 1.) LDA / 1.) THF, hexane, -70 deg C, 30 min, 2.) THF, hexane, RT, overnight

3: 10percent methanol. citric acid / 3 h / Ambient temperature

4: 70 percent / PPh₃, DEAD / tetrahydrofuran / -25 - 20 °C

With triethylamine; triphenylphosphine; citric acid; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ja980444j

upstream raw materials:

phthalimide

(R)-2-tert-Butoxycarbonylmethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

L-4-hydroxyproline methyl ester hydrochloride

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate