3-(Toluene-4-sulfonyloxyMethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 3-(Toluene-4-sulfonyloxyMethyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 852655-86-8
• Molecular Formula: C₂₀H₂₃NO₅S
• Molecular Weight: 389.472
• Mol file: 852655-86-8.mol

Synonyms:benzyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Chemical Property of 3-(Toluene-4-sulfonyloxyMethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

3-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylicacidbenzylester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(Toluene-4-sulfonyloxyMethyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 4 articles about 3-(Toluene-4-sulfonyloxyMethyl)-pyrrolidine-1-carboxylic acid benzyl 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: 88.0%

p-toluenesulfonyl chloride (98-59-9) + benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (315718-05-9) → benzyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate (852655-86-8)

Guidance literature:

With triethylamine; In dichloromethane; for 3h;

Reference yield: 87.0%

4-(((benzyloxy)carbonyl)amino)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate → benzyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate (852655-86-8)

Guidance literature:

With boron trifluoride diethyl etherate; orthobenzoic acid trimethyl ester; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0036-1588750

Reference yield:

benzyl (4-hydroxy-3-(hydroxymethyl)butyl)carbamate → benzyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate (852655-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate; orthobenzoic acid trimethyl ester / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; boron trifluoride diethyl etherate; triethylamine; orthobenzoic acid trimethyl ester; In dichloromethane;

DOI:10.1055/s-0036-1588750

upstream raw materials:

p-toluenesulfonyl chloride

benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Downstream raw materials:

3-cyanomethyl-pyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Park, Heemin,Kwon, Yongseok,Shin, Jae Eui,Kim, Woo-Jung,Hwang, Soonho,Lee, Seokwoo,Kim, Sanghee. "Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions". . p. 2761 - 2767. Retrieved 2017/06/13.
• 2、 -. "AZAINDOLE RETINOIC ACID RECEPTOR-RELATED ORPHAN RECEPTOR MODULATORS AND USES THEREOF". Paragraph 110. . Retrieved 2016/02/18.