lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate
• CAS No.: 1370656-25-9
• Molecular Formula: C₂₀H₂₄N₃O₂*Li
• Molecular Weight: 345.37
• Mol file: 1370656-25-9.mol

Synonyms:lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate

Chemical Property of lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate

There total 4 articles about lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-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: 90.0%

(S)-methyl 1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-29-3) → lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-25-9)

Guidance literature:

With lithium hydroxide; In methanol; for 3h; Reflux;

DOI:10.1016/j.tet.2012.02.031

Reference yield:

(S)-methyl 1-((6-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-26-0) → lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-25-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

2.2: -78 - 0 °C

3.1: sodium tris(acetoxy)borohydride / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide / methanol / 3 h / Reflux

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;

DOI:10.1016/j.tet.2012.02.031

Reference yield:

(S)-methyl 1-((6-(hydroxymethyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-27-1) → lithium (S)-1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate (1370656-25-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

1.2: -78 - 0 °C

2.1: sodium tris(acetoxy)borohydride / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide / methanol / 3 h / Reflux

With oxalyl dichloride; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; lithium hydroxide; In methanol; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation;

DOI:10.1016/j.tet.2012.02.031

upstream raw materials:

(S)-1-phenyl-ethylamine

(S)-methyl 1-((6-formylpyridin-2-yl)methyl)pyrrolidine-2-carboxylate

(S)-methyl 1-((6-(((S)-1-phenylethylamino)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate

(S)-methyl 1-((6-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)methyl)pyrrolidine-2-carboxylate