(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester

Base Information

• Chemical Name: (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester
• CAS No.: 215168-87-9
• Molecular Formula: C₃₁H₃₉NO₈
• Molecular Weight: 553.653
• Mol file: 215168-87-9.mol

Synonyms:(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester

Chemical Property of (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester

There total 7 articles about (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester 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: 71.0%

(1R)-1-[3-[2-(1,1-dimethylethoxy)-2-oxoethoxy]phenyl-3-(4-methoxyphenyl)-1-propanyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate (215168-81-3) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester (215168-87-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h; Acid hydrolysis;

DOI:10.1016/S0968-0896(98)00125-4

Reference yield:

3-Hydroxyacetophenone (121-71-1) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester (215168-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / aq. KOH / ethanol / 16 h / 20 °C

2: 46 percent / H₂ / Lindlar catalyst / aq. methanol / 6 h / 2068.59 - 2585.74 Torr

3: 91 percent / K₂CO₃ / acetone / 20 h / 20 °C

4: 57 percent / (+)-DIP-chloride / tetrahydrofuran / -20 °C

5: 87 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

6: 71 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 20 °C / Acid hydrolysis

With dmap; potassium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; B-chlorodiisopinocampheylborane; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 1: Condensation / 2: Hydrogenation / 3: Alkylation / 4: Reduction / 5: Condensation / 6: Hydrolysis;

DOI:10.1016/S0968-0896(98)00125-4

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propyl ester (215168-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / aq. KOH / ethanol / 16 h / 20 °C

2: 46 percent / H₂ / Lindlar catalyst / aq. methanol / 6 h / 2068.59 - 2585.74 Torr

3: 91 percent / K₂CO₃ / acetone / 20 h / 20 °C

4: 57 percent / (+)-DIP-chloride / tetrahydrofuran / -20 °C

5: 87 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

6: 71 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 20 °C / Acid hydrolysis

With dmap; potassium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; B-chlorodiisopinocampheylborane; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 1: Condensation / 2: Hydrogenation / 3: Alkylation / 4: Reduction / 5: Condensation / 6: Hydrolysis;

DOI:10.1016/S0968-0896(98)00125-4

upstream raw materials:

(1R)-1-[3-[2-(1,1-dimethylethoxy)-2-oxoethoxy]phenyl-3-(4-methoxyphenyl)-1-propanyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate

3-Hydroxyacetophenone

4-methoxy-benzaldehyde

(2E)-1-(3-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one