methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Base Information

Chemical Name:methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate
CAS No.:1263197-96-1
Molecular Formula:C₁₇H₂₃N₃O₇S
Molecular Weight:413.452
Hs Code.:

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

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

Chemical Property:

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

There total 12 articles about methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)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:

: methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]piperidine-3-carboxylate

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 1263197-96-1
methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 ℃; for 1.5h;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester

: 1263197-96-1
methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: C₂₈H₂₇F₆N₃O₃S / tetrahydrofuran / 24 h / -20 °C

2: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4: triethylamine / dichloromethane / 1 h / 20 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 1 h / 20 °C

6: dichloromethane / 2 h / 20 °C

7: N-chloro-succinimide / dichloromethane / 2 h / 20 °C

8: 18 h / 60 °C

9: hydrogenchloride / dichloromethane; water / 4 h / 40 °C

10: thionyl chloride / 1 h / 20 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; C₂₈H₂₇F₆N₃O₃S; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 2: |Curtius Rearrangement;
DOI:10.1016/j.bmcl.2012.09.103

Reference yield:

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

: 1263197-96-1
methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C

2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3: triethylamine / dichloromethane / 1 h / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 1 h / 20 °C

5: dichloromethane / 2 h / 20 °C

6: N-chloro-succinimide / dichloromethane / 2 h / 20 °C

7: 18 h / 60 °C

8: hydrogenchloride / dichloromethane; water / 4 h / 40 °C

9: thionyl chloride / 1 h / 20 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 1: |Curtius Rearrangement;
DOI:10.1016/j.bmcl.2012.09.103