dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

Base Information

Chemical Name:dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate
CAS No.:406502-92-9
Molecular Formula:C₁₆H₂₄NO₄P
Molecular Weight:325.345
Hs Code.:

Synonyms:dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

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Chemical Property of dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

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Technology Process of dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

There total 7 articles about dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate 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: 40.0%

: 406502-86-1
dimethyl (2R,6S,7R)-(-)-[7-(4-methoxy-phenyl)-2-methyl-1-aza-bicyclo-[4.1.0]hept-3-en-6-yl] phosphonate

: 406502-92-9
dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 2h;
DOI:10.1021/ol017289p

Reference yield:

: 2004-70-8,17410-45-6,25212-15-1,64940-84-7
1-methylbuta-1,3-diene

: 406502-92-9
dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / toluene / 16 h / 20 °C

2: 40 percent / H₂ / Pd/C / methanol / 2 h

With hydrogen; palladium on activated charcoal; In methanol; toluene; 1: Diels-Alder reaction;
DOI:10.1021/ol017289p

Reference yield:

: 158109-77-4
(S,E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfinamide

: 406502-92-9
dimethyl (2R,6S,7R)-(-)-[7-(4-methoxyphenyl)-2-methyl-1-aza-bicyclo[4.1.0]hept-6-yl] phosphonate

Guidance literature:: Multi-step reaction with 6 steps

1: 51 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

2: 82 percent / n-BuLi / tetrahydrofuran; cyclohexane / -78 - 20 °C

3: 79 percent / MeMgBr / tetrahydrofuran; diethyl ether / 2 h / -78 °C

4: 68 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 89 percent / toluene / 16 h / 20 °C

6: 40 percent / H₂ / Pd/C / methanol / 2 h

With n-butyllithium; oxalyl dichloride; methylmagnesium bromide; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; toluene; 4: Swern oxidation / 5: Diels-Alder reaction;
DOI:10.1021/ol017289p