(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

Base Information

Chemical Name:(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate
CAS No.:1013097-82-9
Molecular Formula:C₁₉H₂₃Cl₂NO₃
Molecular Weight:384.303
Hs Code.:

Synonyms:(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

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Chemical Property of (1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

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Technology Process of (1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

There total 6 articles about (1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate 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: 46.0%

: (+/-)-(1,1-dimethylethyl) 6-(3,4-dichlorophenyl)-1-(hydroxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

: 74-88-4
methyl iodide

: 1013097-82-9
(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

: (1,1-dimethylethyl) (1R,6S)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

Guidance literature:: (+/-)-(1,1-dimethylethyl) 6-(3,4-dichlorophenyl)-1-(hydroxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate; With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 0.25h; Large scale reaction;

methyl iodide; In dimethyl sulfoxide; at 20 ℃; for 2.25h; optical yield given as %ee; Large scale reaction;
DOI:10.1021/op100139f

Reference yield:

: 1,1-dimethylethyl (1S,6R/1R,6S)-6-(3,4-dichlorophenyl)-1-(methoxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

: 1013097-82-9
(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

: (1,1-dimethylethyl) (1R,6S)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

Guidance literature:: In n-heptane; isopropyl alcohol; Purification / work up;

Reference yield:

: 938183-66-5
1-(1,1-dimethylethyl) 3-ethyl 4-(3,4-dichlorophenyl)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

: 1013097-82-9
(1,1-dimethylethyl) (1S,6R)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

: (1,1-dimethylethyl) (1R,6S)-6-(3,4-dichlorophenyl)-1-(methyloxymethyl)-3-azabicyclo[4.1.0]hept-4-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium tert-butoxide / 1-methyl-pyrrolidin-2-one / 0 - 20 °C / Large scale reaction

2.1: methanol; lithium borohydride / tetrahydrofuran / 1.67 h / 40 °C / Large scale reaction

3.1: potassium hydroxide / dimethyl sulfoxide / 0.25 h / 20 °C / Large scale reaction

3.2: 2.25 h / 20 °C / Large scale reaction

With methanol; lithium borohydride; potassium hydroxide; lithium tert-butoxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dimethyl sulfoxide;
DOI:10.1021/op100139f