benzyl 3-nitroazetidine-1-carboxylate

Base Information

• Chemical Name: benzyl 3-nitroazetidine-1-carboxylate
• CAS No.: 1379079-50-1
• Molecular Formula: C₁₁H₁₂N₂O₄
• Molecular Weight: 236.227
• Mol file: 1379079-50-1.mol

Synonyms:benzyl 3-nitroazetidine-1-carboxylate

Chemical Property of benzyl 3-nitroazetidine-1-carboxylate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-nitroazetidine-1-carboxylate

There total 2 articles about benzyl 3-nitroazetidine-1-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: 40.0%

benzyl 3-iodoazetidine-1-carboxylate (939759-26-9) → benzyl 3-nitroazetidine-1-carboxylate (1379079-50-1)

Guidance literature:

With 3,5-dihydroxyphenol; urea; sodium nitrite; In N,N-dimethyl-formamide; at 50 ℃; for 19h;

DOI:10.1039/c2cc32225k

Reference yield:

1-Benzyloxycarbonyl-3-hydroxyazetidine (128117-22-6) → benzyl 3-nitroazetidine-1-carboxylate (1379079-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / -20 - 20 °C

2: sodium iodide / acetone / 2 h / 20 °C

3: 3,5-dihydroxyphenol; urea; sodium nitrite / N,N-dimethyl-formamide / 19 h / 50 °C

With pyridine; 3,5-dihydroxyphenol; urea; sodium iodide; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/c2cc32225k

Reference yield: 93.0%

benzyl 3-nitroazetidine-1-carboxylate (1379079-50-1) + tert-butyl 4-chlorobenzylidenecarbamate (779342-75-5) → (R)-benzyl 3-((tert-butoxycarbonylamino)(phenyl)methyl)-3-nitroazetidine-1-carboxylate (1379079-51-2)

Guidance literature:

tert-butyl 4-chlorobenzylidenecarbamate; With CHF₃O₃S*C₃₂H₃₈N₆O₂; In toluene; at 20 ℃;

benzyl 3-nitroazetidine-1-carboxylate; In toluene; at -20 ℃; for 20h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c2cc32225k

upstream raw materials:

benzyl 3-iodoazetidine-1-carboxylate

1-Benzyloxycarbonyl-3-hydroxyazetidine

Downstream raw materials:

(S)-benzyl 3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)azetidine-1-carboxylate

(R)-benzyl 3-((tert-butoxycarbonylamino)(phenyl)methyl)-3-nitroazetidine-1-carboxylate

Refernces