(2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine

Base Information

• Chemical Name: (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine
• CAS No.: 1611470-51-9
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.273
• Mol file: 1611470-51-9.mol

Synonyms:(2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine

Chemical Property of (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine

There total 4 articles about (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine 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: 96.0%

1-tert-butyl 2-methyl (2S,5R)-5-phenylpyrrolidine-1,2-dicarboxylate → (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine (1611470-51-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 17h; Inert atmosphere; Reflux;

DOI:10.1039/c4cc02429j

Reference yield:

(S)-methyl 2-((tert-butoxycarbonyl)amino)-5-oxo-5-phenylpentanoate (1611470-49-5) → (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine (1611470-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

1.3: 72 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c4cc02429j

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → (2S,5R)-2-hydroxymethyl-1-methyl-5-phenylpyrrolidine (1611470-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 18 h / -30 - 20 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

2.2: 16 h / 0 - 20 °C / Inert atmosphere

2.3: 72 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c4cc02429j

upstream raw materials:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

phenylmagnesium chloride

(S)-methyl 2-((tert-butoxycarbonyl)amino)-5-oxo-5-phenylpentanoate

Downstream raw materials:

(2S,5R)-2-(methylaminomethyl)-1-methyl-5-phenylpyrrolidine