(3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid

Base Information

• Chemical Name: (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid
• CAS No.: 75821-65-7
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 75821-65-7.mol

Synonyms:(3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid

Chemical Property of (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid

There total 7 articles about (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic 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: 97.0%

(3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester (56151-98-5) → (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid (75821-65-7)

Guidance literature:

In sodium hydroxide; ethanol; at 15 ℃; for 12h; Product distribution;

DOI:10.1016/S0040-4020(01)83119-7

Reference yield: 93.0%

(3R,4S)-(-)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester (56151-97-4) → (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid (75821-65-7)

Guidance literature:

With sodium hydroxide; In ethanol; at 15 ℃; for 12h;

DOI:10.1016/S0040-4020(01)83119-7

Reference yield:

(3R,4S)-1-<2-(3,4-dimethoxyphenyl)-2-hydroxyethyl>-3-ethyl-4-piperidineacetic acid ethyl ester (56151-95-2,75821-63-5,75821-64-6,109785-67-3,109785-69-5) → (3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid (75821-65-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.)(ethylenedinitrilo)tetraacetic acid disodium salt dihydrate and Hg(OAc)2; 2.) anhyd. K₂CO₃ / 1.) 1percent aq. AcOH, reflux, 1.5h; 2.) EtOH, RT, 5h

2: H₂ / 10percent Pd-C / ethanol; aq. HClO₄ / 20 h / 3040 Torr

3: 93 percent / aq. NaOH / ethanol / 12 h / 15 °C

With sodium hydroxide; mercury(II) diacetate; hydrogen; edetate disodium; potassium carbonate; palladium on activated charcoal; In perchloric acid; ethanol;

DOI:10.1016/S0040-4020(01)83119-7

upstream raw materials:

(3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

(3R,4S)-(-)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

cinchonine

(3R,4S)-(+)-1-(3,4-dimethoxyphenacyl)-3-ethyl-4-piperidineacetic acid ethyl ester

Downstream raw materials:

(3S,4S)-(+)-1-(3,4-dimethoxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

Refernces