(-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate

Base Information

• Chemical Name: (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate
• CAS No.: 1394979-17-9
• Molecular Formula: C₁₅H₂₁NO₂
• Molecular Weight: 247.337
• Mol file: 1394979-17-9.mol

Synonyms:(-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate

Chemical Property of (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate

There total 1 articles about (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-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: 75.0%

1-chloro-2-iodoethane (624-70-4) + tert-butyl crotonate (3246-27-3) + C12H20NSi(1-)*Li(1+) → (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate (1394979-17-9) + (-)-tert-butyl (2R,3R)-1-benzyl-3-methylaziridine-2-carboxylate (1394979-18-0)

Guidance literature:

C₁₂H₂₀NSi^(1-)*Li⁽¹⁺⁾; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In toluene; for 0.583333h;

tert-butyl crotonate; In toluene; at -78 ℃; for 1.63h;

1-chloro-2-iodoethane; enantioselective reaction; Further stages;

DOI:10.1021/jo301495a

Reference yield: 71.0%

(-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate (1394979-17-9) → (+)-tert-butyl (2S,3R)-3-methylaziridine-2-carboxylate (937375-79-6,790658-85-4)

Guidance literature:

With 10% Pd/C; hydrogen; In methanol; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1021/jo301495a

Reference yield:

(-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate (1394979-17-9) → tert-butyl (S)-3-methyl-2H-azirine-2-carboxylate (181369-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 10% Pd/C; hydrogen / methanol / 5 h / 20 °C / 760.05 Torr

2: oxalyl dichloride; triethylamine / dimethyl sulfoxide

With oxalyl dichloride; 10% Pd/C; hydrogen; triethylamine; In methanol; dimethyl sulfoxide;

DOI:10.1021/jo301495a

upstream raw materials:

1-chloro-2-iodoethane

tert-butyl crotonate

Downstream raw materials:

(+)-tert-butyl (2S,3R)-3-methylaziridine-2-carboxylate

tert-butyl (S)-3-methyl-2H-azirine-2-carboxylate