N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

Base Information

Chemical Name:N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide
CAS No.:1267579-89-4
Molecular Formula:C₂₀H₂₃F₃N₂O₂S₃
Molecular Weight:476.608
Hs Code.:

Synonyms:N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

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Chemical Property of N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

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Technology Process of N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

There total 10 articles about N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide 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: 94.0%

: 1267580-06-2
(2S, 4R)-tert-butyl-2-(bis(p-tolylthio)methyl)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate

: 1267579-89-4
N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;
DOI:10.1002/ejoc.201001211

Reference yield:

: 1267579-99-6
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

: 1267579-89-4
N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

2.1: sodium azide / N,N-dimethyl-formamide / 20 - 70 °C

3.1: triphenylphosphine / tetrahydrofuran / 2 h

3.2: 3 h / 80 °C

4.1: dmap; triethylamine / dichloromethane / 0.5 h / -76 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

With dmap; sodium azide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201001211

Reference yield:

: 1267580-02-8
(2S, 4R)-tert-butyl 4-azido-2-(bis(p-tolylthio)methyl)pyrrolidine-1-carboxylate

: 1267579-89-4
N-((3R, 5S)-5-(bis(p-tolylthio)methyl)pyrrolidin-3-yl)-1, 1, 1-trifluoromethanesulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine / tetrahydrofuran / 2 h

1.2: 3 h / 80 °C

2.1: dmap; triethylamine / dichloromethane / 0.5 h / -76 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

With dmap; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201001211