methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Base Information

Chemical Name:methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate
CAS No.:1192603-92-1
Molecular Formula:C₁₉H₁₈FN₃O₃
Molecular Weight:355.369
Hs Code.:

Synonyms:methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

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Chemical Property of methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

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Technology Process of methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

There total 4 articles about methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-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:

: 3939-09-1,103496-86-2
2,4-difluorobenzonitrile

: C₁₂H₁₆N₂O₃

: 1192603-92-1
methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Guidance literature:: With lithium carbonate; In dimethyl sulfoxide; at 100 ℃; for 2h;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 1030899-57-0
benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate

: 1192603-92-1
methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: n-butyllithium / hexane; diethyl ether / -78 - 20 °C / Inert atmosphere

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / 60 °C

3: hydrogen; 10 % palladium on carbon / methanol / 3 h / 20 °C

4: lithium carbonate / dimethyl sulfoxide / 2 h / 100 °C

With 10 % palladium on carbon; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; hydrogen; lithium carbonate; triethylamine; In methanol; diethyl ether; hexane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 151004-19-2
(4S,5S)-5-methyl-4-hydroxy-2-oxopyrrolidine

: 1192603-92-1
methyl 5-[(2S,3R)-1-(4-cyano-3-fluorophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium bis(2-methoxyethoxy)aluminum dihydride / toluene; tetrahydrofuran / 4 h / 0 - 70 °C

1.2: 20 °C

1.3: 18 h / 0 - 20 °C

2.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / acetonitrile / 20 h / 20 °C / Molecular sieve

3.1: n-butyllithium / hexane; diethyl ether / -78 - 20 °C / Inert atmosphere

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / 60 °C

5.1: hydrogen; 10 % palladium on carbon / methanol / 3 h / 20 °C

6.1: lithium carbonate / dimethyl sulfoxide / 2 h / 100 °C

With 10 % palladium on carbon; n-butyllithium; tetrapropylammonium perruthennate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium bis(2-methoxyethoxy)aluminum dihydride; hydrogen; lithium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1016/j.bmc.2012.11.001