(R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate

Base Information

• Chemical Name: (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate
• CAS No.: 1446422-46-3
• Molecular Formula: C₁₄H₂₀NO₅P
• Molecular Weight: 313.29
• Mol file: 1446422-46-3.mol

Synonyms:(R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate

Chemical Property of (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate

There total 7 articles about (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate 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:

benzyl 3-methoxyphenyl carbonate (1023285-98-4) + dimethyl pyrrolidine-2-phosphonate (869855-90-3) → (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate (1446422-46-3) + (S)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate + (S)-dimethyl pyrrolidine-2-phosphonate

Guidance literature:

With Candida antarctica lipase type A, immobilized NZL-101; In tert-butyl methyl ether; at 30 ℃; for 84h; Solvent; enantioselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.1016/j.tetasy.2015.10.016

Reference yield:

benzyl 3-methoxyphenyl carbonate (1023285-98-4) + p-toluenesulfonyl chloride (98-59-9) + dimethyl pyrrolidine-2-phosphonate (869855-90-3) → (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate (1446422-46-3) + (S)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate + dimethyl N-tosylpyrrolidine-2-phosphonate

Guidance literature:

benzyl 3-methoxyphenyl carbonate; dimethyl pyrrolidine-2-phosphonate; With Candida antarctica lipase type A, immobilized NZL-101; In tert-butyl methyl ether; at 30 ℃; for 84h; Inert atmosphere; Enzymatic reaction;

p-toluenesulfonyl chloride; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Solvent; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.10.016

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate (1446422-46-3) + (S)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - -40 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / 2 h / 20 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 12 h / -20 - 20 °C / Inert atmosphere

5.1: 250 x 20 mm Chiralpak^? IC column / chloroform; hexane; acetone / Resolution of racemate

With boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; acetone;

DOI:10.1016/j.tetasy.2015.10.016

upstream raw materials:

diazomethane

C₄H₁₀NO₂P

benzyl chloroformate

benzyl 3-methoxyphenyl carbonate