methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Base Information

Chemical Name:methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate
CAS No.:1263198-55-5
Molecular Formula:C₂₆H₃₁FN₄O₇S
Molecular Weight:562.619
Hs Code.:

Synonyms:methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

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Chemical Property of methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

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Technology Process of methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

There total 8 articles about methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-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: 84.0%

: 1263198-53-3
methyl (3S,5R)-5-{[2-(5-fluoro-2-methylanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

: 598-21-0
2-Bromoacetyl bromide

: 1263198-55-5
methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 20 - 40 ℃; for 6.25h; Cooling with ice;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: 534572-20-8
(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

: 1263198-55-5
methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 7 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

7.1: triethylamine / dichloromethane / 6.25 h / 20 - 40 °C / Cooling with ice

With hydrogenchloride; palladium 10% on activated carbon; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: 1448902-04-2
1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

: 1263198-55-5
methyl (3S,5R)-5-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 6 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

6.1: triethylamine / dichloromethane / 6.25 h / 20 - 40 °C / Cooling with ice

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2013.06.057