(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one
CAS No.:1415505-90-6
Molecular Formula:C₁₈H₂₅BrN₂O₂
Molecular Weight:381.313
Hs Code.:

Synonyms:(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

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Chemical Property of (3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

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Technology Process of (3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

There total 5 articles about (3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-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: 67.0%

: 1415505-82-6
(3R,4S)-1-allyl-3-benzyloxy-4-{(E)-[((1,1-dimethylethyl)imino)methyl]}azetidin-2-one

: 1415505-90-6
(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

Guidance literature:: (3R,4S)-1-allyl-3-benzyloxy-4-{(E)-[((1,1-dimethylethyl)imino)methyl]}azetidin-2-one; With bromine; In dichloromethane; at -78 ℃; for 2h;

With sodium hydrogencarbonate; In ethanol; at -78 ℃; for 1h; Reflux;
DOI:10.1016/j.tet.2011.09.136

Reference yield:

: Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-amine

: 1415505-90-6
(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C

2.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 4 h / Heating

3.1: sodium periodate; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C

4.1: magnesium sulfate / dichloromethane / 1 h / 20 °C

5.1: bromine / dichloromethane / 2 h / -78 °C

5.2: 1 h / -78 °C / Reflux

With sodium periodate; bromine; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2011.09.136

Reference yield:

: 253599-41-6
(+)-(3R,4R)-3-benzyloxy-1-(2-propenyl)-4-oxoazetidine-2-carbaldehyde

: 1415505-90-6
(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: magnesium sulfate / dichloromethane / 1 h / 20 °C

2.1: bromine / dichloromethane / 2 h / -78 °C

2.2: 1 h / -78 °C / Reflux

With bromine; magnesium sulfate; In dichloromethane;
DOI:10.1016/j.tet.2011.09.136