methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate
• CAS No.: 1427086-46-1
• Molecular Formula: C₁₅H₁₈N₂O₆
• Molecular Weight: 322.318
• Mol file: 1427086-46-1.mol

Synonyms:methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate

Chemical Property of methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate

Chemical Property:

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Technology Process of methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate

There total 1 articles about methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-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: 85.0%

methyl (2S)-pyrrolidine carboxylate (2577-48-2) + methyl 4-bromomethyl-3-nitrobenzoate (88089-94-5) → methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate (1427086-46-1)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1007/s11172-012-0166-7

Reference yield: 51.0%

methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate (1427086-46-1) → methyl 1-[2-amino-4-(methoxycarbonyl)benzyl]pyrrolidine-2-carboxylate (1427086-47-2)

Guidance literature:

With hydrogenchloride; ferrous(II) sulfate heptahydrate; ammonium hydroxide; In methanol; water; at 65 - 90 ℃; for 0.416667h;

DOI:10.1007/s11172-012-0166-7

Reference yield:

methyl 1-[4-(methoxycarbonyl)-2-nitrobenzyl]pyrrolidine-2-carboxylate (1427086-46-1) → methyl 10-benzyl-11-oxo-11a-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1.1: ferrous(II) sulfate heptahydrate; hydrogenchloride; ammonium hydroxide / water; methanol / 0.42 h / 65 - 90 °C

2.1: acetic acid / 13 h / Reflux

3.1: sodium hydride / N,N-dimethyl-formamide / 25 °C / Inert atmosphere; Cooling with ice

3.2: 1 h / 25 °C / Inert atmosphere

4.1: methanol / 95 h / 30 °C

With hydrogenchloride; ferrous(II) sulfate heptahydrate; ammonium hydroxide; sodium hydride; In methanol; water; acetic acid; N,N-dimethyl-formamide; 4.1: |Stevens Rearrangement;

DOI:10.1007/s11172-012-0166-7

upstream raw materials:

methyl (2S)-pyrrolidine carboxylate

methyl 4-bromomethyl-3-nitrobenzoate

Downstream raw materials:

methyl 1-[2-amino-4-(methoxycarbonyl)benzyl]pyrrolidine-2-carboxylate

methyl 10-benzyl-11-oxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1c][1,4]benzodiazepine-8-carboxylate