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

Base Information

• Chemical Name: 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate
• CAS No.: 1263198-12-4
• Molecular Formula: C₂₄H₃₄ClN₃O₅
• Molecular Weight: 480.004

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

Chemical Property of 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate

There total 10 articles about 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate 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:

di-tert-butyl dicarbonate (24424-99-5) + methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylate (1263198-15-7) → 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate (1263198-12-4)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmc.2013.06.057

Reference yield:

(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid (534572-20-8) → 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate (1263198-12-4)

Guidance literature:

Multi-step reaction with 9 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

8.1: caesium carbonate; thiophenol / acetonitrile / 2.5 h / 20 °C

9.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 20 °C

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

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) → 1-tert-butyl 3-methyl (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-1,3-dicarboxylate (1263198-12-4)

Guidance literature:

Multi-step reaction with 8 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

7.1: caesium carbonate; thiophenol / acetonitrile / 2.5 h / 20 °C

8.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 20 °C

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; caesium carbonate; acetic acid; thiophenol; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

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-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-5-{[(1R)-1-(3-chlorophenyl)propyl]carbamoyl}piperidine-1-carboxylate

tert-butyl (3R,5S)-3-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-5-{[(1R)-1-(4-chlorophenyl)propyl]carbamoyl}piperidine-1-carboxylate

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

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

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