methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate
• CAS No.: 1095278-82-2
• Molecular Formula: C₁₁H₁₁NO₄
• Molecular Weight: 221.213
• Mol file: 1095278-82-2.mol

Synonyms:methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate

Chemical Property of methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate

There total 3 articles about methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate 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%

methanol (67-56-1) + 4-methoxyphenyl-(1S,2S)-(Z)-1-nitro-2-phenylcyclopropanecarboxylate (1196666-36-0) → methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate (1095278-82-2)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ja201237j

Reference yield:

methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate (1036637-32-7) + carbon dioxide (124-38-9,18923-20-1) + dimethyl sulfate (77-78-1) → methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate (1095278-82-2)

Guidance literature:

methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate; With sodium hydroxide; In ethanol; at 20 ℃; for 2h; Inert atmosphere;

carbon dioxide; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Molecular sieve; Inert atmosphere;

dimethyl sulfate; In N,N-dimethyl-formamide; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.113

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → methyl (1S,2S)-1-nitro-2-phenylcyclopropanecarboxylate (1095278-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver hexafluoroantimonate; iodosylbenzene; sodium carbonate; C₂₅H₃₀N₂O₂; copper(l) chloride / benzene / 3 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: sodium hydroxide / ethanol / 2 h / 20 °C / Inert atmosphere

2.2: 12 h / 20 °C / Molecular sieve; Inert atmosphere

2.3: 0.75 h / Inert atmosphere

With silver hexafluoroantimonate; iodosylbenzene; sodium carbonate; C₂₅H₃₀N₂O₂; copper(l) chloride; sodium hydroxide; In ethanol; benzene;

DOI:10.1016/j.tet.2011.05.113

upstream raw materials:

methanol

4-methoxyphenyl-(1S,2S)-(Z)-1-nitro-2-phenylcyclopropanecarboxylate

methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate

carbon dioxide

Downstream raw materials:

methyl (4R)-4-(2,3-dihydro-1H-indol-1-yl)-2-nitro-4-phenylbutanoate

C₁₁H₁₃NO₂

(Z)-2,3-methanophenylalanine methyl ester

methyl (1R,2R)-1-amino-2-phenylcyclopropanecarboxylate