1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine

Base Information

• Chemical Name: 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine
• CAS No.: 1440956-27-3
• Molecular Formula: C₁₂H₁₄F₃NO₂S
• Molecular Weight: 293.31
• Mol file: 1440956-27-3.mol

Synonyms:1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine

Chemical Property of 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine

There total 3 articles about 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine 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: 51.0%

3-iodo-1-(p-methylbenzenesulfonyl)pyrrolidine + Togni's reagent II (887144-94-7) → 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine (1440956-27-3)

Guidance literature:

With 2-pyrrolidinon; (1,2-dimethoxyethane)dichloronickel(II); lithium methanolate; 2,4,7,9-tetraphenyl-1,10-phenanthroline; copper(l) chloride; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane; In N,N-dimethyl-formamide; at 25 ℃; for 6.66667h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/acs.orglett.8b02005

Reference yield:

1-tosylpyrrolidin-3-ylboronic acid (1440956-52-4) + (trifluoromethyl)trimethylsilane (81290-20-2) → 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine (1440956-27-3) + 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole (16851-72-2)

Guidance literature:

With potassium fluoride; 3,4,7,8-Tetramethyl-o-phenanthrolin; 2C₇H₇O₃S^(1-)*Cu⁽²⁺⁾*C₆H₆; silver(I) 4-methylbenzenesulfonate; silver fluoride; In N,N-dimethyl-formamide; at 50 ℃; for 24h; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201206681

Reference yield:

C17H26BNO4S (1440956-22-8) → 1-(toluene-4-sulfonyl)-3-trifluoromethyl-pyrrolidine (1440956-27-3) + 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole (16851-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / ethanol / 20 - 80 °C

2: 2C₇H₇O₃S^(1-)*Cu⁽²⁺⁾*C₆H₆; 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; potassium fluoride; silver(I) 4-methylbenzenesulfonate / N,N-dimethyl-formamide / 24 h / 50 °C / Glovebox; Inert atmosphere

With hydrogenchloride; potassium fluoride; 3,4,7,8-Tetramethyl-o-phenanthrolin; 2C₇H₇O₃S^(1-)*Cu⁽²⁺⁾*C₆H₆; silver(I) 4-methylbenzenesulfonate; silver fluoride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201206681

upstream raw materials:

1-tosylpyrrolidin-3-ylboronic acid

(trifluoromethyl)trimethylsilane

C₁₇H₂₆BNO₄S

Togni's reagent II