(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

Base Information

Chemical Name:(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate
CAS No.:848476-33-5
Molecular Formula:C₂₃H₂₉NO₆
Molecular Weight:415.486
Hs Code.:

Synonyms:(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

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Chemical Property of (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

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Technology Process of (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

There total 6 articles about (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(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: 90.0%

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

: 848476-42-6
3-((3R,3aR,7R,7aS)-octahydro-1,5-dioxo-3-phenyl-1H-isoindol-7-yl)propyl formate

: 848476-33-5
(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

Guidance literature:: With dmap; In dichloromethane; for 18h;
DOI:10.1021/ja042415g

Reference yield:

: 100-07-2
4-methoxy-benzoyl chloride

: 848476-33-5
(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / triethylamine / CH₂Cl₂ / 18 h / 0 °C

2.1: NaH / dimethylformamide / 12 h

2.2: 75 percent / dimethylformamide / 24 h

3.1: 34 percent / (R)-N-isopropyl-1-phenylethylamine lithium salt / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

4.1: tert-butyl lithium / diethyl ether; hexane / -78 - 20 °C

4.2: Li[Cu(CN)Me] / diethyl ether; hexane / 20 °C

4.3: 79 percent / diethyl ether; hexane / 2 h / -78 °C

5.1: 90 percent / 0.5 h / Heating

6.1: 90 percent / DMAP / CH₂Cl₂ / 18 h

With dmap; lithium R-(-)-N-isopropyl-1-phenylethyl amide; tert.-butyl lithium; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja042415g

Reference yield:

: 454479-63-1
N-(1-methyl-1-phenylethyl)-4-methoxybenzamide

: 848476-33-5
(1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 12 h

1.2: 75 percent / dimethylformamide / 24 h

2.1: 34 percent / (R)-N-isopropyl-1-phenylethylamine lithium salt / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

3.1: tert-butyl lithium / diethyl ether; hexane / -78 - 20 °C

3.2: Li[Cu(CN)Me] / diethyl ether; hexane / 20 °C

3.3: 79 percent / diethyl ether; hexane / 2 h / -78 °C

4.1: 90 percent / 0.5 h / Heating

5.1: 90 percent / DMAP / CH₂Cl₂ / 18 h

With dmap; lithium R-(-)-N-isopropyl-1-phenylethyl amide; tert.-butyl lithium; sodium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja042415g