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

Base Information

Chemical Name:benzyl (2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidine-1-carboxylate
CAS No.:1192609-28-1
Molecular Formula:C₁₈H₁₉BrN₂O₃
Molecular Weight:391.264
Hs Code.:

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

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Chemical Property of benzyl (2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

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Technology Process of benzyl (2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

There total 3 articles about benzyl (2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidine-1-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: 36.0%

: 624-28-2
2,5-dibromopyridine

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

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

Guidance literature:: With n-butyllithium; In diethyl ether; hexane; at -78 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With n-butyllithium; tetrapropylammonium perruthennate; sodium bis(2-methoxyethoxy)aluminum dihydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With n-butyllithium; tetrapropylammonium perruthennate; sodium bis(2-methoxyethoxy)aluminum dihydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile;
DOI:10.1016/j.bmc.2012.11.001