methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate
• CAS No.: 400724-21-2
• Molecular Formula: C₂₀H₃₇NO₅Si
• Molecular Weight: 399.603
• Mol file: 400724-21-2.mol

Synonyms:methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate

Chemical Property of methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate

There total 1 articles about methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate (400724-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: 100 percent / imidazole / dimethylformamide / 20 °C

3.1: LDA / tetrahydrofuran; hexane / 1 h / -30 - -20 °C

3.2: 35 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b105238c

Reference yield:

methyl (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate (400724-21-2) → methyl (2R,4R)-1-(o-bromobenzoyl)-4-(tert-butyldimethylsilyloxy)-2-(prop-2-enyl)pyrrolidine-2-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: TMSI / acetonitrile / 0.25 h / 0 °C

2: 18 mg / Et₃N; DMAP / benzene / 20 °C

With dmap; trimethylsilyl iodide; triethylamine; In acetonitrile; benzene;

DOI:10.1039/b105238c

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride