(S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide

Base Information

• Chemical Name: (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide
• CAS No.: 148460-96-2
• Molecular Formula: C₂₁H₃₂N₂O₅
• Molecular Weight: 392.495
• Mol file: 148460-96-2.mol

Synonyms:(S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide

Chemical Property of (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide

There total 8 articles about (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide 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:

2-6-dimethoxybenzoic acid (1466-76-8) → (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide (148460-96-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) SOCl₂, DMF / 1) toluene, 2) CH₂Cl₂, overnight

2: trifluoroacetic anhydride / 1) 40 deg C, 8 h, 2) rt, 16 h

3: m-chloroperbenzoic acid, p-TsOH / CHCl₃ / 24 h / Ambient temperature

4: aq. HCl / acetone / 6 h / 60 °C

5: 89 percent / CHCl₃; trifluoroacetic acid / 16 h / 60 °C

6: 67 percent / Zn, aq. HOAc / tetrahydrofuran / 3.5 h / ice bath

7: SOCl₂, DMF / toluene / 1.5 h / 60 °C

8: CH₂Cl₂

With hydrogenchloride; thionyl chloride; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; zinc; In tetrahydrofuran; dichloromethane; chloroform; acetone; toluene; trifluoroacetic acid;

DOI:10.1021/jo00065a015

Reference yield:

2,2,2-Trichloroethyl 2,6-Dimethoxybenzoate (148460-81-5) → (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide (148460-96-2)

Guidance literature:

Multi-step reaction with 7 steps

1: trifluoroacetic anhydride / 1) 40 deg C, 8 h, 2) rt, 16 h

2: m-chloroperbenzoic acid, p-TsOH / CHCl₃ / 24 h / Ambient temperature

3: aq. HCl / acetone / 6 h / 60 °C

4: 89 percent / CHCl₃; trifluoroacetic acid / 16 h / 60 °C

5: 67 percent / Zn, aq. HOAc / tetrahydrofuran / 3.5 h / ice bath

6: SOCl₂, DMF / toluene / 1.5 h / 60 °C

7: CH₂Cl₂

With hydrogenchloride; thionyl chloride; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; zinc; In tetrahydrofuran; dichloromethane; chloroform; acetone; toluene; trifluoroacetic acid;

DOI:10.1021/jo00065a015

Reference yield:

2,6-Dimethoxy-3-pivaloylbenzoic Acid (148461-01-2) → (S)-2,6-Dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-pivaloylbenzamide (148460-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, DMF / toluene / 1.5 h / 60 °C

2: CH₂Cl₂

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; toluene;

DOI:10.1021/jo00065a015

upstream raw materials:

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-6-dimethoxybenzoic acid

2,2,2-Trichloroethyl 2,6-Dimethoxybenzoate

2,6-Dimethoxy-3-pivaloylbenzoic Acid

Downstream raw materials:

(S)-N-<(1-Ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

(S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

(S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-6-methoxysalicylamide