ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

Base Information

Chemical Name:ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate
CAS No.:1257251-14-1
Molecular Formula:C₁₉H₂₅NO₅
Molecular Weight:347.411
Hs Code.:

Synonyms:ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

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Chemical Property of ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

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Technology Process of ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

There total 10 articles about ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-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: 52.0%

: 623-73-4
diazoacetic acid ethyl ester

: 1257251-10-7
(4S)-1-(2,4-dimethoxybenzyl)-4-methyl-3,4-dihydropyridin-2(1H)-one

: ethyl (4R)-2-[1-(2,4-dimethoxybenzyl)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridin-2-yl]acetate

: 1257251-14-1
ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

Guidance literature:: With rhodium(II) acetate dimer; In dichloromethane; at 20 ℃; for 5h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201000863

Reference yield: 23.0%

: 623-73-4
diazoacetic acid ethyl ester

: 1257251-10-7
(4S)-1-(2,4-dimethoxybenzyl)-4-methyl-3,4-dihydropyridin-2(1H)-one

: 1257251-14-1
ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

: ethyl (1S*,5S*,6S*,7R*)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

Guidance literature:: With copper(I) triflate; 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline]; In dichloromethane; at 20 ℃; for 12h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201000863

Reference yield:

: 32365-96-1,68702-74-9,86462-82-0
methyl 3-(R)-methyl-5-hydroxypentanoate

: ethyl (4R)-2-[1-(2,4-dimethoxybenzyl)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridin-2-yl]acetate

: 1257251-14-1
ethyl (1S,5S,6S,7S)-2-(2,4-dimethoxybenzyl)-5-methyl-3-oxo-2-azabicyclo[4.1.0]heptane-7-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene / 3 h / Reflux

2: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 5 h / 0 - 20 °C / Inert atmosphere

3: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C

4: rhodium(II) acetate dimer / dichloromethane / 5 h / 20 °C / Inert atmosphere

With rhodium(II) acetate dimer; sulfur trioxide pyridine complex; methanesulfonyl chloride; triethylamine; In dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1002/ejoc.201000863