tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

Base Information

Chemical Name:tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate
CAS No.:1293305-94-8
Molecular Formula:C₂₂H₃₁NO₄Si
Molecular Weight:401.578
Hs Code.:

Synonyms:tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

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Chemical Property of tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

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Technology Process of tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

There total 5 articles about tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-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: 86.0%

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

: 1293306-08-7
(3S,3aS,7S,7aR)-3-phenyl-7-(trimethylsilyl)hexahydro-1H-isoindole-1,5(6H)-dione

: 1293305-94-8
tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1039/c1cc00048a

Reference yield:

: 72659-59-7,116593-04-5
lithium R-(-)-N-isopropyl-1-phenylethyl amide

: 1293305-94-8
tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium; copper(l) cyanide; lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 0.25 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / 1 h / Reflux; Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; methyllithium; copper(l) cyanide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1039/c1cc00048a

Reference yield:

: 1293306-05-4
C₂₉H₄₁NO₂Si₂

: 1293305-94-8
tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogenchloride / tetrahydrofuran; water / 0.25 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / 1 h / Reflux; Inert atmosphere

3: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1039/c1cc00048a