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

Base Information

• Chemical Name: methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate
• CAS No.: 1263198-04-4
• Molecular Formula: C₂₅H₂₉ClN₄O₇S
• Molecular Weight: 565.047

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

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

Chemical Property:

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

There total 15 articles about methyl (3S,5R)-5-[4-(2-chlorophenyl)-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: 78.0%

methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-01-1) + 2-Bromoacetyl bromide (598-21-0) → methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-04-4)

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:

2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester → methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-04-4)

Guidance literature:

Multi-step reaction with 13 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

11: acetic acid / toluene / 2 h / 110 °C

12: sodium cyanoborohydride / 6 h / 20 °C

13: triethylamine / dichloromethane / 5 h / 0 - 40 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; C₂₈H₂₇F₆N₃O₃S; diphenylphosphoranyl azide; sodium cyanoborohydride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 2: |Curtius Rearrangement;

DOI:10.1016/j.bmcl.2012.09.103

Reference yield:

methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263197-96-1) → methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate (1263198-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / toluene / 2 h / 110 °C

2: sodium cyanoborohydride / 6 h / 20 °C

3: triethylamine / dichloromethane / 5 h / 0 - 40 °C

With sodium cyanoborohydride; acetic acid; triethylamine; In dichloromethane; toluene;

DOI:10.1016/j.bmcl.2012.09.103

upstream raw materials:

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

C₁₆H₂₆N₂O₆

C₁₇H₂₁N₃O₈S

C₁₉H₂₉N₃O₈S

Downstream raw materials:

C₂₈H₃₈ClN₅O₂*C₄H₄O₄

(3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylic acid

C₂₉H₃₈ClN₅O₆S

C₃₁H₄₂ClN₅O₆S

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