(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

Base Information

Chemical Name:(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester
CAS No.:155530-48-6
Molecular Formula:C₂₇H₃₅NO₅Si
Molecular Weight:481.664
Hs Code.:

Synonyms:(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

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Chemical Property of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

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Technology Process of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

There total 8 articles about (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-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: 84.0%

: 449143-41-3
(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

: 155530-48-6
(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: With hydrogenchloride; sodium tetrahydroborate; In ethanol; at -10 ℃; for 1h;
DOI:10.1016/S0040-4039(00)75792-3

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 155530-48-6
(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

3.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

4.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

With dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/ja0202964

Reference yield:

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 155530-48-6
(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-dihydropyrrole-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

4.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

5.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja0202964