2-Pyrrolidinone,4-hydroxy-, (4R)-

Base Information

• Chemical Name: 2-Pyrrolidinone,4-hydroxy-, (4R)-
• CAS No.: 22677-21-0
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: DERIVATION
• Mol file: 22677-21-0.mol

Synonyms:2-Pyrrolidinone,4-hydroxy-, (R)- (8CI);(4R)-4-Hydroxy-2-pyrrolidinone;(4R)-4-Hydroxypyrrolidin-2-one;(R)-4-Hydroxy-2-pyrrolidinone;(R)-4-Hydroxypyrrolidin-2-one;

Chemical Property of 2-Pyrrolidinone,4-hydroxy-, (4R)-

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 9.26E-07mmHg at 25°C
• Melting Point: 156-160 °C
• Refractive Index: 1.513
• Boiling Point: 363.6 °C at 760 mmHg
• PKA: 13.62±0.20(Predicted)
• Flash Point: 173.7 °C
• PSA: 49.33000
• Density: 1.292 g/cm³
• LogP: -0.80400
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly), Methanol (Slightly), Water (Sparingly)
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-4-Hydroxy-2-pyrrolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: The (R)-enantiomer intermediate in the preparation of Oxiracetam (R)-(+)-4-Hydroxy-2-pyrrolidinone intermediate in the preparation of Oxiracetam. Also used as enantiomeric intermediate for the asymmetric single isomeric drugs including antitumor, anesthetic, antipasmodic, anti-inflammatory or anti-HIV activity products.

Technology Process of 2-Pyrrolidinone,4-hydroxy-, (4R)-

There total 19 articles about 2-Pyrrolidinone,4-hydroxy-, (4R)- 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%

4-Trimethylsilyloxy-1H-pyrrolidin-2one (68252-20-0) → 4-hydroxy-2-oxopyrrolidine (22677-21-0,25747-41-5,62624-29-7,68108-18-9,96820-00-7)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; for 0.0833333h;

Reference yield: 92.0%

4-Hydroxy-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-one → 4-hydroxy-2-oxopyrrolidine (22677-21-0,25747-41-5,62624-29-7,68108-18-9,96820-00-7)

Guidance literature:

With methanesulfonic acid; In toluene; for 6h; Heating;

DOI:10.1016/j.tetlet.2006.01.019

Reference yield: 82.0%

ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4,86728-85-0,87068-18-6,90866-33-4) → (R)-4-hydroxy-2-pyrrolidinone (22677-21-0,96820-00-7)

Guidance literature:

With ammonium hydroxide; at 80 ℃; for 3h;

DOI:10.1016/S0040-4020(01)91362-6

upstream raw materials:

DL-4-amino-3-hydroxybutyric acid

4-Trimethylsilyloxy-1H-pyrrolidin-2one

ethyl 4-chloro-3-hydroxybutanoate

methyl 4-chloro-3-hydroxybutanoate

Downstream raw materials:

4-benzoylthio-2-pyrrolidone

4-acetoxy-2-pyrrolidinone

4-benzoyloxy-2-pyrrolidinone

2-Pyrrolidon-4-yl p-Toluenesulfonate

Refernces

• 1、 Haeusler, Johannes. "A Convenient Synthesis of (R)-γ-Amino-β-hydroxybutanoic Acid (GABOB) from Natural (2S,4R)-4-Hydroxyproline (Short Communication)". . p. 865 - 870. Retrieved 1987.
• 2、 Bisol, Tula B.,Bortoluzzi, Adailton J.,Sa, Marcus M.. "Nucleophilic ring-opening of epoxide and aziridine acetates for the stereodivergent synthesis of β-Hydroxy and β-Amino γ-Lactams". experimental part. p. 948 - 962. Retrieved 2011/04/12.
• 3、 Paik, Seunguk,Lee, Jun Young. "Simple and efficient cleavage of the N-(1-phenylethyl) unit of carboxamides with methanesulfonic acid". . p. 1813 - 1815. Retrieved 2007/10/03.