(3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione

Base Information

• Chemical Name: (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione
• CAS No.: 819054-53-0
• Molecular Formula: C₂₃H₂₁BrN₂O₅
• Molecular Weight: 485.334
• Mol file: 819054-53-0.mol

Synonyms:(3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione

Chemical Property of (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione

There total 3 articles about (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione 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: 72.0%

(3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-7-[(tert-butyl)dimethylsilyloxy]-2,3,3a,4,5,6,7,8,8a,8b-decahydro-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione (819054-67-6) → (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione (819054-53-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1002/hlca.200490225

Reference yield: 14.0%

4-bromo-benzaldehyde (1122-91-4) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + N-(3,4-methylenedioxybenzyl)maleimide (182191-39-5) → (3aS,4R,7R,8aS,8bR)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione (819054-52-9) + (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione (819054-53-0)

Guidance literature:

In acetonitrile; at 90 ℃; for 28h; Title compound not separated from byproducts;

DOI:10.1002/1522-2675(200205)85:5<1210::AID-HLCA1210>3.0.CO;2-T

Reference yield:

(3aS,4R,7R,8aS,8bR)-2-Benzo[1,3]dioxol-5-ylmethyl-4-(4-bromo-phenyl)-7-hydroxy-hexahydro-pyrrolo[3,4-a]pyrrolizine-1,3-dione; compound with (3aR,4S,7R,8aR,8bS)-2-benzo[1,3]dioxol-5-ylmethyl-4-(4-bromo-phenyl)-7-hydroxy-hexahydro-pyrrolo[3,4-a]pyrrolizine-1,3-dione → (3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-2,3,3a,4,5,6,7,8,8a,8b-decahydro-7-hydroxy-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione (819054-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / DMAP / CH₂Cl₂ / 16 h / 25 °C

2: 72 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.200490225

upstream raw materials:

4-bromo-benzaldehyde

4R-4-hydroxyproline

N-(3,4-methylenedioxybenzyl)maleimide

(3aR,4S,7R,8aR,8bS)-2-[(benzo[1,3]dioxol-5-yl)methyl]-4-(4-bromophenyl)-7-[(tert-butyl)dimethylsilyloxy]-2,3,3a,4,5,6,7,8,8a,8b-decahydro-1H-pyrrolo[3,4-a]pyrrolizin-1,3-dione