(S)-4-Hydroxy-2-pyrrolidinone Chemical Properties

Melting point:

156-159 °C (lit.)

alpha 

-41 º (c=% in ethanol)

Boiling point:

363.6±35.0 °C(Predicted)

Density 

1.292±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

pka

13.62±0.20(Predicted)

form 

Solid

color 

White to off-white

optical activity

[α]23/D 43°, c = 1 in ethanol

BRN 

1524192

InChI

1S/C4H7NO2/c6-3-1-4(7)5-2-3/h3,6H,1-2H2,(H,5,7)/t3-/m0/s1

InChIKey

IOGISYQVOGVIEU-VKHMYHEASA-N

SMILES

O[C@@H]1CNC(=O)C1

CAS DataBase Reference

68108-18-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29349990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1

MSDS

• Language:English Provider:SigmaAldrich

(S)-4-Hydroxy-2-pyrrolidinone Usage And Synthesis

Chemical Properties

White crystal

Uses

(S)-(?)-4-Hydroxy-2-pyrrolidinone can be used as a starting material in the preparation of:

• Biologically significant pyrrolo[1,2:1′,2′]azepino[5,6-b]indole derivatives.
• Substituted azepanes by reacting with various aldehydes via photochemical [5+2] cycloaddition.

Uses

The (S)-enantiomer intermediate in the preparation of Oxiracetam

General Description

4-Hydroxy-2-pyrrolidinone is an important building block found in many bioactive compounds like streptopyrrolidine. It can be used as an intermediate in the synthesis of various γ-amino acids (GABA) and substituted 2-pyrrolidinones like cynometrine and cynodine.

Synthesis

10.1 g (100 mmol) of 2-oxiranylacetamide, CuI 0.95 g (5 mmol), cesium carbonate 2 g (200 mmol) was added to 150 ml of ammonia in a saturated solution of methanol, 55 ?? for stirring reaction for 8 h, the reaction solution was concentrated under reduced pressure, 100 ml of water was added, dichloromethane extraction three times, saturated saline washed three times, the phase of ethyl acetate was concentrated under reduced pressure, and petroleum ether recrystallization to obtain (S)-(-)-4-hydroxy-2-pyrrolidinone 8.71g, yield 86.3%, HPLC purity 99.42% (area normalization method), ee value 99.67%.

(S)-4-Hydroxy-2-pyrrolidinone(68108-18-9)Related Product Information

• N-Vinyl-2-pyrrolidone
• CHLOROPHOSPHONAZO III
• 2-Pyrrolidinone
• N-Methyl-2-pyrrolidone
• Povidone iodine
• 4-hydroxypyrrolidin-2-one
• OxiracetaM Related CoMpound 2
• Oxiracetam Related Compound 7
• Oxiracetam
• 2-(2-oxo-2,5-dihydro-1H-pyrrol-1-yl)acetaMide
• Oxiracetam Related Compound 8
• methyl 4-hydroxy-2-oxopyrrolidine-1-acetate
• 2-[(carbamoylmethyl)amino]acetamide
• Oxiracetam Related Compound 5
• 4-Hydroxy-2-oxo-1-pyrrolidineacetic acid
• (4S)-4-hydroxy-2-oxo-1-Pyrrolidineacetic acid Methyl ester
• Polyvinylpyrrolidone
• ethyl 4-hydroxy-2-oxopyrrolidine-1-acetate