methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Base Information

• Chemical Name: methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate
• CAS No.: 1263198-33-9
• Molecular Formula: C₂₄H₃₂N₄O₆S
• Molecular Weight: 504.607

Synonyms:methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Chemical Property of methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

There total 7 articles about methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-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: 98.0%

methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263197-96-1) + o-toluidine (95-53-4) → methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-33-9)

Guidance literature:

methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate; o-toluidine; With acetic acid; In toluene; at 130 ℃; for 4h; Dean-Stark;

With sodium tris(acetoxy)borohydride; In toluene; at 20 ℃; for 16h; Dean-Stark;

DOI:10.1016/j.bmc.2013.06.057

Reference yield:

(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid (534572-20-8) → methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-33-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; diphenylphosphoranyl azide / toluene / 1.5 h / 90 °C

1.2: 3.5 h / 90 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C

3.1: N,N-dimethyl-formamide; water / 24 h / 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C

5.1: sodium hydrogencarbonate / water; 1,4-dioxane / 1.5 h / 0 °C

6.1: acetic acid / toluene / 4 h / 130 °C / Dean-Stark

6.2: 16 h / 20 °C / Dean-Stark

With hydrogenchloride; palladium 10% on activated carbon; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2013.06.057

Reference yield:

1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate (1448902-04-2) → methyl (3S,5R)-5-{[1,1-dimethyl-2-(2-methylanilino)ethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C

2.1: N,N-dimethyl-formamide; water / 24 h / 20 °C

3.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C

4.1: sodium hydrogencarbonate / water; 1,4-dioxane / 1.5 h / 0 °C

5.1: acetic acid / toluene / 4 h / 130 °C / Dean-Stark

5.2: 16 h / 20 °C / Dean-Stark

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2013.06.057

upstream raw materials:

(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

1-tert-butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate

1-tert-Butyl 3-methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]piperidine-1,3-dicarboxylate

Downstream raw materials:

tert-butyl (3R,5S)-3-[2,2-dimethyl-4-(o-tolyl)-5-oxopiperazin-1-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

C₂₀H₂₉N₃O₃

C₂₉H₄₀FN₅O₂

1-tert-butyl 3-methyl (3S,5R)-5-[2,2-dimethyl-4-(o-tolyl)-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate

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