N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine

Base Information

• Chemical Name: N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine
• CAS No.: 1301189-18-3
• Molecular Formula: C₁₆H₂₃N₃O
• Molecular Weight: 273.378

Synonyms:N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine

Chemical Property of N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine

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Technology Process of N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine

There total 5 articles about N₁-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine 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:

N-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-2-nitroaniline (1301189-16-1) → N1-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine (1301189-18-3)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; at 20 ℃; under 1810.07 Torr;

Reference yield:

1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidinecarboxylate (199175-10-5) → N1-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine (1301189-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 70 °C

2: hydrogenchloride / dichloromethane / 2 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

4: hydrogen / palladium 10% on activated carbon / ethanol / 20 °C / 1810.07 Torr

With hydrogenchloride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; In ethanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

tert-butyl (3R)-3-cyano-1-pyrrolidinecarboxylate (132945-76-7) → N1-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-1,2-benzenediamine (1301189-18-3)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogen / ethanol; water / 3102.97 Torr

2: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 70 °C

3: hydrogenchloride / dichloromethane / 2 h / 20 °C

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

5: hydrogen / palladium 10% on activated carbon / ethanol / 20 °C / 1810.07 Torr

With hydrogenchloride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; In ethanol; dichloromethane; water; dimethyl sulfoxide;

upstream raw materials:

1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidinecarboxylate

tert-butyl (3R)-3-cyano-1-pyrrolidinecarboxylate

1,1-dimethylethyl (3S)-3-{[(3-methyl-2-nitrophenyl)amino]methyl}-1-pyrrolidinecarboxylate

N-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-methyl-2-nitroaniline

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