methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate

Base Information

• Chemical Name: methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate
• CAS No.: 233281-62-4
• Molecular Formula: C₂₈H₃₃N₃O₅
• Molecular Weight: 491.587

Synonyms:methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate

Chemical Property of methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate

Chemical Property:

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Technology Process of methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate

There total 3 articles about methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate 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: 99.0%

3-cyano-1-(2-formylethenyl)benzene (98116-49-5) + methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anthranilate (179756-40-2) → methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate (233281-62-4)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; acetic acid; at 20 ℃; for 14h;

DOI:10.1016/S0968-0896(02)00462-5

Reference yield:

methyl 2-amino-5-hydroxybenzoate (1882-72-0) → methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate (233281-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / PPh₃; DEAD / tetrahydrofuran / 96 h / 20 °C

2: 99 percent / NaB(OAc)3H / CH₂Cl₂; acetic acid / 14 h / 20 °C

With sodium tris(acetoxy)borohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetic acid; 1: Mitsunobu condensation;

DOI:10.1016/S0968-0896(02)00462-5

Reference yield:

t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-[(E)-3-cyanocinnamyl]anthranilate (233281-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / PPh₃; DEAD / tetrahydrofuran / 96 h / 20 °C

2: 99 percent / NaB(OAc)3H / CH₂Cl₂; acetic acid / 14 h / 20 °C

With sodium tris(acetoxy)borohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetic acid; 1: Mitsunobu condensation;

DOI:10.1016/S0968-0896(02)00462-5

upstream raw materials:

3-cyano-1-(2-formylethenyl)benzene

methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anthranilate

methyl 2-amino-5-hydroxybenzoate

t-butyl 4-hydroxy piperidine-1-carboxylate

Downstream raw materials:

7-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-1-[(E)-3-cyanocinnamyl]-1H-1,4-benzodiazepine-2,5(3H,4H)-dione

methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-(tert-butoxycarbonylsulfamoyl)-N-[3-(3-cyanophenyl)propyl]anthranilate

3-{3-[2,2,4-trioxo-6-(piperidin-4-yloxy)-3,4-dihydro-2H-2λ⁶-benzo[1,2,6]thiadiazin-1-yl]-propenyl}-benzamidine

1-[(E)-3-cyanocinnamyl]-6-[(4-piperidyl)oxy]-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide

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