(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

Chemical Name:(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate
CAS No.:1219963-29-7
Molecular Formula:C₂₀H₂₈F₃NO₆SSi
Molecular Weight:495.592
Hs Code.:

Synonyms:(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

There total 8 articles about (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-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: 91.0%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 197079-39-3
(S)-benzyl 2-(tert-butyldimethylsilyloxy)methyl-4-oxo-pyrrolidine-1-carboxylate

: 1219963-29-7
(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: (S)-benzyl 2-(tert-butyldimethylsilyloxy)methyl-4-oxo-pyrrolidine-1-carboxylate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran;
DOI:10.1021/jm901722v

Reference yield: 78.0%

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: 197079-39-3
(S)-benzyl 2-(tert-butyldimethylsilyloxy)methyl-4-oxo-pyrrolidine-1-carboxylate

: 1219963-29-7
(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: (S)-benzyl 2-(tert-butyldimethylsilyloxy)methyl-4-oxo-pyrrolidine-1-carboxylate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.666667h; Inert atmosphere;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; at -78 ℃; for 1.16667h; Inert atmosphere;
DOI:10.1021/jacs.1c03529

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 1219963-29-7
(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 7 h / 23 °C / Inert atmosphere

2.1: sulfuric acid / 12 h / Reflux; Inert atmosphere

3.1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; water / 22 h / 17 - 23 °C / Inert atmosphere

4.1: triethylamine / toluene / 18 h / 60 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 2.5 h / 0 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

6.2: 1.17 h / -78 °C / Inert atmosphere

With sodium hypochlorite; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sulfuric acid; sodium hexamethyldisilazane; sodium hydrogencarbonate; triethylamine; lithium chloride; potassium bromide; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/jacs.1c03529