(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:210534-34-2
Molecular Formula:C₂₂H₃₄BrNO₄Si
Molecular Weight:484.506
Hs Code.:

Synonyms:(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl 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: 70.0%

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 18620-02-5
(4-bromophenyl)magnesium bromide

: 210534-34-2
(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With copper(l) iodide; chloro-trimethyl-silane; In N,N,N,N,N,N-hexamethylphosphoric triamide; at -20 ℃;
DOI:10.1021/ja980513u

Reference yield: 84.0%

: 67-64-1
acetone

: 210534-34-2
(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 210534-35-3
(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With magnesium(II) perchlorate; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/ja980513u

Reference yield:

: 210534-34-2
(2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: (3R,4R,5S)-5-Hydroxymethyl-3-isopropyl-4-(4-nonyl-phenyl)-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / LiN(TMS)2, Mg(ClO₄)2 / tetrahydrofuran

2: 1.) Et₃NSO₂NCO₂Me, 2.) DBU / 1.) C₆H₆, 60 deg C, 2.) toluene, reflux

3: 85 percent / 1.) PdCl₂(PPh₃)4, CuI, Et₃N / dimethylformamide / 80 °C

4: 96 percent / Bu₄NF / tetrahydrofuran

5: 100 percent / H₂ / 10percent Pd/C

6: 94 percent / TFA / CH₂Cl₂

With copper(l) iodide; magnesium(II) perchlorate; Burgess Reagent; tetrakis(triphenylphosphine)palladium dichloride; tetrabutyl ammonium fluoride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja980513u