tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate
• CAS No.: 946594-20-3
• Molecular Formula: C₂₃H₃₅ClN₂O₄
• Molecular Weight: 438.995
• Mol file: 946594-20-3.mol

Synonyms:tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Chemical Property of tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

There total 6 articles about tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate 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: 95.0%

(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (690660-22-1) + Boc-D-Val-OH (22838-58-0) → tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (946594-20-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃;

DOI:10.1016/j.bmcl.2013.04.079

Reference yield:

tert-butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate (324769-06-4) → tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (946594-20-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -78 - -60 °C

1.2: 2 h / -78 - -60 °C

2.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C

3.1: butanone; water / 20 °C / Reflux

4.1: sodium hydroxide / water

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C

5.2: 20 h / 20 °C

With hydrogenchloride; n-butyllithium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; benzotriazol-1-ol; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; butanone;

Reference yield:

4-(4-chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester (475085-56-4) → tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (946594-20-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C

2.1: butanone; water / 20 °C / Reflux

3.1: sodium hydroxide / water

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C

4.2: 20 h / 20 °C

With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; benzotriazol-1-ol; In 1,4-dioxane; dichloromethane; water; butanone;

upstream raw materials:

(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Boc-D-Val-OH

tert-butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

4-(4-chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloric acid salt

1-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-cyclopentylurea

(R)-1-sec-butyl-3-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)urea