(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

Base Information

Chemical Name:(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one
CAS No.:761457-12-9
Molecular Formula:C₁₉H₂₃NO₅
Molecular Weight:345.395
Hs Code.:

Synonyms:(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

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Chemical Property of (3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

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Technology Process of (3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

There total 4 articles about (3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-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: 91.0%

: C₂₁H₂₇NO₅

: 761457-12-9
(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

Guidance literature:: Grubbs catalyst first generation; In toluene; for 7h; Heating;
DOI:10.1002/adsc.200600502

Reference yield: 76.0%

: 106-95-6
allyl bromide

: 220574-31-2
(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone

: 761457-12-9
(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

Guidance literature:: allyl bromide; (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone; With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 20 ℃; for 16h;

Grubbs catalyst first generation; In toluene; for 7h; Further stages.; Heating;
DOI:10.1016/j.tetlet.2004.06.130

Reference yield:

: 153463-32-2
(S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione

: 761457-12-9
(3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-phenyl)-5-oxa-2-aza-spiro[3.5]non-7-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / indium powder; NH₄Cl / tetrahydrofuran; H₂O

2: 83 percent / tetrabutylammonium iodide; aq. NaOH / CH₂Cl₂ / 20 h / 20 °C

3: 91 percent / [Cl₂(PCy₃)2Ru=CHPh] / toluene / 7 h / Heating

With indium; sodium hydroxide; tetra-(n-butyl)ammonium iodide; ammonium chloride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; toluene; 1: Barbier(-type) reaction;
DOI:10.1002/adsc.200600502