[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester

Base Information

• Chemical Name: [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester
• CAS No.: 1369205-85-5
• Molecular Formula: C₂₁H₂₉NO₃S
• Molecular Weight: 375.532
• Mol file: 1369205-85-5.mol

Synonyms:[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester

Chemical Property of [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester

There total 11 articles about [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl 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: 88.4%

(1R)-toluene-4-sulfonic acid 3-[1-(2-dimethylamino-1-methylethyl)propenyl]phenyl ester (1369206-03-0) → [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester (1369205-85-5)

Guidance literature:

(1R)-toluene-4-sulfonic acid 3-[1-(2-dimethylamino-1-methylethyl)propenyl]phenyl ester; With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In ethanol; water; for 36h; under 4413.43 Torr;

With sodium carbonate; In water; at 20 ℃; pH=7 - 8; Product distribution / selectivity;

Reference yield:

[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester oxalic acid (1369205-86-6) → [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester (1369205-85-5)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; for 0.5h;

Reference yield:

rac-3-(dimethylamino)-1-(3-hydroxyphenyl)-2-methylpropan-1-one (1343471-61-3) → [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester (1369205-85-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / dichloromethane / 1 h / 30 - 35 °C

2.1: O,O'-dibenzoyl-L-tartaric acid / ethyl acetate / 5 h / 10 - 20 °C / Cooling

2.2: 1 h / 20 - 25 °C

3.1: tetrahydrofuran / 3 h / 25 - 30 °C

4.1: hydrogenchloride / water / 24 h / Reflux

4.2: 10 - 15 °C

5.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 36 h / 4413.43 Torr

5.2: 20 °C / pH 7 - 8

With hydrogenchloride; hydrogen; potassium carbonate; O,O'-dibenzoyl-L-tartaric acid; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate;

upstream raw materials:

p-toluenesulfonyl chloride

1-(3-hydroxyphenyl)propan-1-one

rac-3-(dimethylamino)-1-(3-hydroxyphenyl)-2-methylpropan-1-one

toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester

Downstream raw materials:

tapentadol

tapentadol hydrochloride

[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester oxalic acid

Refernces

• 1、 -. "PROCESS FOR PREPARING L-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVE". . . Retrieved 2012/04/10.