(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

Base Information

Chemical Name:(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one
CAS No.:645396-53-8
Molecular Formula:C₂₂H₂₂N₂O₄
Molecular Weight:378.428
Hs Code.:

Synonyms:(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

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Chemical Property of (2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

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Technology Process of (2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

There total 5 articles about (2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one 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: 98.0%

: 182316-18-3
(5S)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide

: 645396-51-6
2-[(indol-3-yl)methyl]prop-2-en-1-ol

: 645396-53-8
(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

Guidance literature:: With magnesium bromide; In dichloromethane; at 20 ℃; for 84h;
DOI:10.1021/jo040296h

Reference yield:

: 87438-91-3
ethyl 2-((1H-indol-3-yl)methyl)acrylate

: 645396-53-8
(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / DIBAL-H / CH₂Cl₂; hexane / -78 - 20 °C

2: CH₂Cl₂ / 360 h / 20 °C

With diisobutylaluminium hydride; In hexane; dichloromethane;
DOI:10.1021/jo040296h

Reference yield:

: 182316-18-3
(5S)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide

: 645396-52-7
3-(2-hydroxymethyl-allyl)-indole-1-carboxylic acid tert-butyl ester

: 645396-53-8
(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

: 645396-54-9
(2S,5S,8aS)-2-[(1-(tertbutoxycarbonyl)indol-3-yl)methyl]-2-(hydroxymethyl)-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

Guidance literature:: With magnesium bromide; In dichloromethane; at 20 ℃; for 96h; Title compound not separated from byproducts.;
DOI:10.1039/b306791m