(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

Base Information

Chemical Name:(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid
CAS No.:1263198-18-0
Molecular Formula:C₂₃H₃₂ClN₃O₅
Molecular Weight:465.977
Hs Code.:

Synonyms:(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

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Chemical Property of (3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

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Technology Process of (3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

There total 11 articles about (3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid 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: 100.0%

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

: 1263198-18-0
(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

Guidance literature:: With lithium hydroxide monohydrate; In tetrahydrofuran; water; for 2h; 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

: 1263198-18-0
(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 10 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

10.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / Cooling with ice

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

: 1263198-18-0
(3S,5R)-1-tert-butoxycarbonyl-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]piperidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 9 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

9.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / Cooling with ice

With hydrogenchloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; caesium carbonate; acetic acid; thiophenol; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.bmc.2013.06.057