(2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine

Base Information

• Chemical Name: (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine
• CAS No.: 125023-61-2
• Molecular Formula: C₂₀H₂₆N₂O
• Molecular Weight: 310.439
• Mol file: 125023-61-2.mol

Synonyms:(2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine

Chemical Property of (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine

There total 8 articles about (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine 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:

(2R,5S)-2-Dimethylaminomethyl-5-(hydroxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid ethyl ester (125023-63-4) → (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine (125023-61-2)

Guidance literature:

With potassium hydroxide; water; In methanol; at 120 ℃; for 16h; Yield given;

DOI:10.1021/jo00290a002

Reference yield:

(S)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid diethyl ester → (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine (125023-61-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.1percent p-CH₃C₆H₄SO₃H / 23 °C

2: 62 percent / stannic chloride / CH₂Cl₂ / 24 h / -40 °C

3: 81 percent / H₂ / W-II Raney nickel / methanol; various solvent(s) / 16 h / 23 °C / 760 Torr

4: tetrahydrofuran / 16 h / 23 °C

5: 13.5percent KOH, water / methanol / 16 h / 120 °C

With potassium hydroxide; water; hydrogen; tin(IV) chloride; toluene-4-sulfonic acid; W-II Raney nickel; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00290a002

Reference yield:

(S)-5-Methoxy-pyrrolidine-1,2-dicarboxylic acid diethyl ester (125023-58-7,125132-88-9) → (2S,5R)-(-)-2-(hydroxydiphenylmethyl)-5-((dimethylamino)methyl)pyrrolidine (125023-61-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / stannic chloride / CH₂Cl₂ / 24 h / -40 °C

2: 81 percent / H₂ / W-II Raney nickel / methanol; various solvent(s) / 16 h / 23 °C / 760 Torr

3: tetrahydrofuran / 16 h / 23 °C

4: 13.5percent KOH, water / methanol / 16 h / 120 °C

With potassium hydroxide; water; hydrogen; tin(IV) chloride; W-II Raney nickel; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00290a002

upstream raw materials:

D-Glutamic acid

(2R,5S)-2-Dimethylaminomethyl-5-(hydroxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid ethyl ester

(S)-5-Methoxy-pyrrolidine-1,2-dicarboxylic acid diethyl ester

ethyl (S)-N-(ethoxycarbonyl)pyroglutamate