(S)-(1-Benzylpyrrolidin-3-yl)methanol

Base Information

• Chemical Name: (S)-(1-Benzylpyrrolidin-3-yl)methanol
• CAS No.: 78914-69-9
• Molecular Formula: C12H17 N O
• Molecular Weight: 191.273
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90363858
• Wikidata: Q82147612
• Mol file: 78914-69-9.mol

Synonyms:(S)-(1-Benzylpyrrolidin-3-yl)methanol;78914-69-9;(S)-1-Benzyl-beta-prolinol;(S)-(1-Benzyl-pyrrolidin-3-yl)-methanol;[(3S)-1-benzylpyrrolidin-3-yl]methanol;SCHEMBL5968994;(S)-1-BENZYL-b-PROLINOL;DTXSID90363858;(S)-1-Benzyl-3-pyrrolidinemethanol;MFCD09608006;AKOS006331270;((S)-1-Benzylpyrrolidin-3-yl)methanol;AC-29341;AS-81896;TS-02702;AM20120539;CS-0171340;A864948

Chemical Property of (S)-(1-Benzylpyrrolidin-3-yl)methanol

Chemical Property:

• Vapor Pressure: 0.00255mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 274.9°C at 760 mmHg
• PKA: 14.93±0.10(Predicted)
• Flash Point: 115.4°C
• PSA: 23.47000
• Density: 1.082g/cm³
• LogP: 1.43870
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 191.131014166
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

98%min ^*data from raw suppliers

(S)-(1-Benzylpyrrolidin-3-yl)methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1CO)CC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@H]1CO)CC2=CC=CC=C2

Technology Process of (S)-(1-Benzylpyrrolidin-3-yl)methanol

There total 8 articles about (S)-(1-Benzylpyrrolidin-3-yl)methanol 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: 95.0%

(S)-1-Benzyl-3-benzyloxymethyl-pyrrolidine (192213-99-3) → (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride (78914-69-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h;

DOI:10.1021/jo9701905

Reference yield:

(R)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one (172796-28-0) → (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride (78914-69-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / LAH / tetrahydrofuran / 0 deg C to reflux

2: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / Et₃N / dioxane / 12 h / Heating

4: 95 percent / H₂ / Pd/C / methanol / 24 h

With dmap; lithium aluminium tetrahydride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo9701905

Reference yield:

(S)-2-Benzyloxymethyl-butane-1,4-diol (192213-97-1) → (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride (78914-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 85 percent / Et₃N / dioxane / 12 h / Heating

3: 95 percent / H₂ / Pd/C / methanol / 24 h

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo9701905

upstream raw materials:

(S)-1-Benzyl-3-benzyloxymethyl-pyrrolidine

(S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid

methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate

Dimethyl itakonate

Downstream raw materials:

(S)-(-)-3-(hydroxymethyl)pyrrolidine

-(+)-methanol

(S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid

(S)-(+)-3-pyrrolidinecarboxylic acid

Refernces

• 1、 Mazzini,Lebreton,Alphand,Furstoss. "Enantiodivergent chemoenzymatic synthesis of (R)- and (S)-β-proline in high optical purity". . p. 5215 - 5218. Retrieved 2007/10/03.