(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

Base Information

Chemical Name:(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile
CAS No.:773143-72-9
Molecular Formula:C₁₆H₁₈N₂O₄
Molecular Weight:302.33
Hs Code.:

Synonyms:(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

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Chemical Property of (3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

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Technology Process of (3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

There total 3 articles about (3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile 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%

: 1001909-49-4
C₁₆H₂₁NO₅

: 7677-24-9
trimethylsilyl cyanide

: 773143-72-9
(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

: 773143-71-8
(3aS,4R,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 20h;
DOI:10.1016/j.tetlet.2007.10.125

Reference yield: 46.0%

: 77-76-9
2,2-dimethoxy-propane

: 773143-70-7
Acetic acid (3S,4S)-4-acetoxy-2-cyano-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester

: 773143-72-9
(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

: 773143-71-8
(3aS,4R,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

Guidance literature:: Acetic acid (3S,4S)-4-acetoxy-2-cyano-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester; With acetyl chloride; In ethanol; at 50 ℃; for 2.5h;

2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In acetone; at 30 ℃; for 2h; Further stages.;
DOI:10.1016/j.tet.2004.06.109

Reference yield:

: (+/-)-(3R,4S)-3,4-diacetoxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione

: 773143-72-9
(3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: (S)-BINAL-H; EtOH / tetrahydrofuran / 17 h / -78 °C

1.2: 68 percent / pyridine / 20 °C

2.1: 100 percent / BF₃*Et₂O / toluene / 1 h / 20 °C

3.1: acetyl chloride / ethanol / 2.5 h / 50 °C

3.2: 46 percent / p-toluenesulfonic acid / acetone / 2 h / 30 °C

With ethanol; (-)-(S)-BINAL-H; boron trifluoride diethyl etherate; acetyl chloride; In tetrahydrofuran; ethanol; toluene;
DOI:10.1016/j.tet.2004.06.109