1H-Isoindole-1,3(2H)-dione, 2-[(3S,5R)-5-hydroxy-2,6-dioxo-3-piperidinyl]-5-(phenylmethoxy)-

Base Information

Chemical Name:1H-Isoindole-1,3(2H)-dione, 2-[(3S,5R)-5-hydroxy-2,6-dioxo-3-piperidinyl]-5-(phenylmethoxy)-
CAS No.:928776-73-2
Molecular Formula:C20H16N2O6
Molecular Weight:380.357
Hs Code.:

Synonyms:

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Chemical Property of 1H-Isoindole-1,3(2H)-dione, 2-[(3S,5R)-5-hydroxy-2,6-dioxo-3-piperidinyl]-5-(phenylmethoxy)-

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Technology Process of 1H-Isoindole-1,3(2H)-dione, 2-[(3S,5R)-5-hydroxy-2,6-dioxo-3-piperidinyl]-5-(phenylmethoxy)-

There total 12 articles about 1H-Isoindole-1,3(2H)-dione, 2-[(3S,5R)-5-hydroxy-2,6-dioxo-3-piperidinyl]-5-(phenylmethoxy)- 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: 100.0%

: 928776-72-1
5-benzyloxy-2-(5-tert-butyldimethylsilyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

: 928776-73-2
5-benzyloxy-2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Guidance literature:: With chloroform; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2.66667h;
DOI:10.1248/cpb.54.1709

Reference yield:

: 928776-65-2
(2S,4R)-tert-butyl 2-carbamoyl-4-tert-butyldimethylsilyloxy-5-oxopyrrolidine-1-carboxylate

: 928776-73-2
5-benzyloxy-2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1: aq. LiOH / tetrahydrofuran / 3 h / 0 °C

2: 660 mg / CDI; DMAP; diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

3: 100 percent / CH₂Cl₂ / 0.5 h / 20 °C

4: 44 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; TEA / CH₂Cl₂ / 24 h / 20 °C

5: 100 percent / tetrabutylammonium fluoride; CHCl₃ / tetrahydrofuran / 2.67 h / 0 - 20 °C

With dmap; lithium hydroxide; chloroform; TEA; tetrabutyl ammonium fluoride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.54.1709

Reference yield:

: 928776-64-1
tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-carbamoylpyrrolidine-1-carboxylate

: 928776-73-2
5-benzyloxy-2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / NaIO₄; RuO₂ / ethyl acetate; H₂O / 3 h / 20 °C

2: aq. LiOH / tetrahydrofuran / 3 h / 0 °C

3: 660 mg / CDI; DMAP; diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

4: 100 percent / CH₂Cl₂ / 0.5 h / 20 °C

5: 44 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; TEA / CH₂Cl₂ / 24 h / 20 °C

6: 100 percent / tetrabutylammonium fluoride; CHCl₃ / tetrahydrofuran / 2.67 h / 0 - 20 °C

With dmap; ruthenium(IV) oxide; lithium hydroxide; sodium periodate; chloroform; TEA; tetrabutyl ammonium fluoride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; ethyl acetate;
DOI:10.1248/cpb.54.1709