Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate
• CAS No.: 861657-91-2
• Molecular Formula: C₁₁H₁₇NO₅
• Molecular Weight: 243.26
• Mol file: 861657-91-2.mol

Synonyms:rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property of Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate

Chemical Property:

• Boiling Point: 361.6±35.0 °C(Predicted)
• PKA: -4.28±0.40(Predicted)
• Density: 1.209±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

1-tert-Butyl2-methyl5-oxopyrrolidine-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate

There total 6 articles about Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl 5-oxopyrrolidine-2-carboxylate (4931-66-2,54571-66-3,64700-65-8) → rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate (861657-91-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield: 70.0%

methanol (67-56-1) + di-tert-butyl dicarbonate (24424-99-5) + Pyroglutamic acid (149-87-1) → rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate (861657-91-2)

Guidance literature:

methanol; Pyroglutamic acid; With thionyl chloride; at 20 - 25 ℃; for 1h;

di-tert-butyl dicarbonate; With dmap; In ethyl acetate; at 20 - 25 ℃; for 3h;

DOI:10.1002/anie.202100922

Reference yield: 40.0%

(+/-)-N-tert-butoxycarbonylproline methyl ester (145681-01-2) → rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate (861657-91-2)

Guidance literature:

(+/-)-N-tert-butoxycarbonylproline methyl ester; With [bis(acetoxy)iodo]benzene; In nitromethane; at 0 ℃;

With tert.-butylhydroperoxide; In decane; nitromethane; at 0 - 25 ℃; for 18h;

DOI:10.1039/c3ra44184a

upstream raw materials:

di-tert-butyl dicarbonate

methyl (S)-pyroglutamate

methyl 5-oxopyrrolidine-2-carboxylate

(+/-)-N-tert-butoxycarbonylproline methyl ester

Downstream raw materials:

1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate

methyl 5-methylpyrrolidine-2-carboxylate

methyl (2R*,5R*)-5-methylpyrrolidine-2-carboxylate

(2S/R,5R/S)-1-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid

Refernces

Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

10.1016/j.tet.2018.11.030

The research focuses on the enantioselective addition of diethylzinc to aldehydes, utilizing 5-cis-substituted proline derivatives as chiral ligands. The purpose of this study was to develop efficient ligands that could provide high enantioselectivity, with the aim of controlling the sense of asymmetric induction through the nature of the exocyclic functional group. The researchers synthesized and evaluated prolinols, prolinamines, and prolinamine sulfonamides, which were derived from methyl Boc-L-pyroglutamate. They found that the additional 5-cis substituent significantly improved chirality transfer, with the best results obtained being up to 99% enantiomeric excess (ee). The study concluded that the sense of asymmetric induction was dependent on the presence of α-substituents and the nature of the exocyclic functionality. The chemicals used in the process included various aldehydes, diethylzinc, and a series of proline derivatives such as 5-cis-substituted prolinols (7), prolinamines (8), and prolinamine sulfonamides (9), which were synthesized from methyl Boc-L-pyroglutamate (10). The researchers also explored the structural and stereochemical aspects of the reactions, providing a detailed discussion on the respective transition states.

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