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

Base Information

Chemical Name:(2S, 4R)-tert-butyl-2-(bis(p-tolylthio)methyl)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate
CAS No.:1267580-06-2
Molecular Formula:C₂₅H₃₁F₃N₂O₄S₃
Molecular Weight:576.725
Hs Code.:

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

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Chemical Property of (2S, 4R)-tert-butyl-2-(bis(p-tolylthio)methyl)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate

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Technology Process of (2S, 4R)-tert-butyl-2-(bis(p-tolylthio)methyl)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate

There total 9 articles about (2S, 4R)-tert-butyl-2-(bis(p-tolylthio)methyl)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate 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: 84.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 1267580-03-9
(2S, 4R)-tert-butyl 4-amino-2-(bis(p-tolylthio)methyl)pyrrolidine-1-carboxylate

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -76 ℃; for 0.5h; Inert atmosphere;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 1267579-95-2
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

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

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

4.1: triphenylphosphine / tetrahydrofuran / 2 h

4.2: 3 h / 80 °C

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

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