methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

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Chemical Name:methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate
CAS No.:1192609-30-5
Molecular Formula:C₂₀H₂₂N₂O₅
Molecular Weight:370.405
Hs Code.:

Synonyms:methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

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Chemical Property of methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

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Technology Process of methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

There total 5 articles about methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-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: 66.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 1192609-28-1
benzyl (2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

: 1192609-30-5
methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine; at 60 ℃;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 1030899-56-9
benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

: 1192609-30-5
methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / acetonitrile / 20 h / 20 °C / Molecular sieve

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

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

With n-butyllithium; tetrapropylammonium perruthennate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 4-methylmorpholine N-oxide; triethylamine; In diethyl ether; hexane; acetonitrile;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1192609-30-5
methyl 5-{(2S,3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-2-methylpyrrolidin-3-yl}pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 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

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