L-Prolinol

Base Information

• Chemical Name: L-Prolinol
• CAS No.: 23356-96-9
• Molecular Formula: C5H11NO
• Molecular Weight: 101.148
• Hs Code.: 29221990
• European Community (EC) Number: 245-605-2
• UNII: L5GD8LDG49
• Nikkaji Number: J9.290H
• Wikipedia: Prolinol
• ChEMBL ID: CHEMBL1916080
• Mol file: 23356-96-9.mol

Synonyms:prolinol;prolinol, (+-)-isomer;prolinol, (S)-isomer

Chemical Property of L-Prolinol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.0423mmHg at 25°C
• Melting Point: 42-44℃
• Refractive Index: 1.4853
• Boiling Point: 211 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 86.1 °C
• PSA: 32.26000
• Density: 0.978 g/cm³
• LogP: 0.05950
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform
• Water Solubility.: Fully miscible in water. Soluble in chloroform.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 101.084063974
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

99% ^*data from raw suppliers

L-Prolinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)CO
• Isomeric SMILES: C1C[C@H](NC1)CO
• Uses: L-Prolinol is an intermediate in the synthesis of Physostigmine and Physostigmine derivative used for treatment of Alzheimer's disease. rac-Prolinol is an intermediate in the synthesis of Physostigmine and Physostigmine derivative used for treatment of Alzheimer''s disease.

Technology Process of L-Prolinol

There total 71 articles about L-Prolinol 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: 100.0%

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9)

Guidance literature:

L-proline; With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.25h; Heating / reflux;

With potassium hydroxide; In tetrahydrofuran; water; for 1.25h; Heating / reflux;

Reference yield: 95.0%

L-Pyroglutamic acid (98-79-3) → (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9)

Guidance literature:

With hydrogen; acetic acid; In water; at 100 ℃; for 20h; under 52505.3 Torr; Pressure; Temperature; Reagent/catalyst; Time; Autoclave;

Reference yield: 90.0%

methyl (2S)-pyrrolidine carboxylate (2577-48-2) → (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Reflux;

upstream raw materials:

ethyl (2S)-pyrrolidine-2-carboxylate

N-Cbz-Prolinol

(2S,1'S)-2-Hydroxymethyl-N-1'-(2-methoxyphenyl)propyl-1-pyrrolidinecarboxamide

L-proline

Downstream raw materials:

(S)-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

{(S)-1-[(E)-2-(Diphenyl-phosphinoyl)-vinyl]-pyrrolidin-2-yl}-methanol

(1'R,2'R,6'S)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

(1'S,2'S,6'R)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

Refernces

Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines by employing polymer-supported reagents: Preparation of DC-81

10.1055/s-2004-834821

The research focuses on the synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines, specifically the natural product DC-81, using polymer-supported reagents. This approach aims to create a combinatorial library of substituted pyrrolo[2,1-c][1,4]benzodiazepine derivatives efficiently and without the need for conventional purification techniques like chromatography. The methodology involves an intramolecular aza-Wittig reaction and utilizes reagents such as L-prolinol, 2-azido benzoic acids, borohydride exchange resin, polymer-supported cyclohexylcarbodiimide, polymer-supported sulfoxide, and polymer-supported TPP. The synthesis process includes coupling reactions, oxidation steps using modified Swern procedure and polymer-supported perruthenate, and intramolecular reductive cyclization. The final product, DC-81, is obtained by debenzylation using Pd/C. Throughout the experiments, various analytical techniques such as 1H NMR, MS (EI), and optical rotation measurements were employed to characterize and confirm the structures of the synthesized compounds.

A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams

10.1021/ol201962n

The research aims to develop a new method for synthesizing a diverse collection of benzofused sultams, which are cyclic sulfonamides with potential applications in drug discovery. The study employs a reaction pairing strategy involving a triad of reactions: sulfonylation, SNAr addition, and Mitsunobu alkylation. By varying the order of these reactions and using different building blocks such as o-fluorobenzenesulfonyl chlorides, amines, and alcohols, the researchers were able to generate a variety of tricyclic and bicyclic benzofused sultams. Key chemicals used include (S)-prolinol, propargylamine, (R)-(t)-3-hydroxypyrrolidine, and 2-piperidinemethanol. The study concludes that this approach allows for rapid and efficient synthesis of diverse sultam scaffolds in just 2-3 steps, making it highly suitable for high-throughput screening (HTS) in drug discovery. The synthesized compounds were found to be structurally diverse and unique compared to existing analogs, as demonstrated through chemical informatics analysis.