1,2-Pyrrolidinedicarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1-(9H-fluoren-9-ylmethyl) ester, (2S,3R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1-(9H-fluoren-9-ylmethyl) ester, (2S,3R)-
• CAS No.: 357916-36-0
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507
• Mol file: 357916-36-0.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1-(9H-fluoren-9-ylmethyl) ester, (2S,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1-(9H-fluoren-9-ylmethyl) ester, (2S,3R)-

There total 8 articles about 1,2-Pyrrolidinedicarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1-(9H-fluoren-9-ylmethyl) ester, (2S,3R)- 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: 68.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,3R)-3-tert-Butoxycarbonylamino-pyrrolidine-2-carboxylic acid → (2S,3R)-3-tert-butoxycarbonylaminopyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (357916-36-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/anie.200250348

Reference yield: 60.0%

(2S,3R)-3-aminopyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (648930-80-7) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-3-tert-butoxycarbonylaminopyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (357916-36-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 17h;

Reference yield:

benzyl (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate (145574-16-9) → (2S,3R)-3-tert-butoxycarbonylaminopyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (357916-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / triethylamine / dimethylformamide; CH₂Cl₂

2: 99 percent / LiOH / tetrahydrofuran; H₂O

3: 93 percent / H₂ / Pd/C / methanol

4: 68 percent / iPr₂NEt / CH₂Cl₂

With lithium hydroxide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200250348

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

benzyl (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

benzyl (1S,5R)-6-(3,4-dimethoxybenzyl)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate