1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-
• CAS No.: 149814-40-4
• Molecular Formula: C16H31NO5Si
• Molecular Weight: 345.511
• Mol file: 149814-40-4.mol

Synonyms:N-Boc-trans-4-tert-butyldimethylsiloxy-L-proline;

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

Chemical Property:

• PSA: 76.07000
• LogP: 3.40870

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-1-(tert-Butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

There total 9 articles about 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,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: 96.0%

1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (114676-91-4) → (2S,4R)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid (149814-40-4)

Guidance literature:

With lithium hydroxide; In methanol; at 45 ℃; for 1h;

DOI:10.1039/b105238c

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid (149814-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 100 percent / imidazole / dimethylformamide / 20 °C

3: 96 percent / aq. LiOH / methanol / 1 h / 45 °C

With 1H-imidazole; dmap; lithium hydroxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b105238c

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,4R)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid (149814-40-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

(+)-menthyl (2S,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylate

(-)-menthyl (2S,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylate

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-((S)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-((R)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester