5-hydroxymethyl-pyrrolidine-2-one

5-hydroxymethyl-pyrrolidine-2-one Property

Melting point:

87 °C

Boiling point:

185-187 °C(Press: 4 Torr)

Density 

1.153±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.35±0.10(Predicted)

Appearance

White to off-white Solid

optical activity

2.3°(C=0.96 g/100ml ETOH)

InChI

InChI=1S/C5H9NO2/c7-3-4-1-2-5(8)6-4/h4,7H,1-3H2,(H,6,8)

InChIKey

HOBJEFOCIRXQKH-UHFFFAOYSA-N

SMILES

N1C(CO)CCC1=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

5-hydroxymethyl-pyrrolidine-2-one Chemical Properties,Usage,Production

Uses

5-(hydroxymethyl)-2-Pyrrolidinone is a building block and an analog of Pramanicin which induces apoptosis in human colon cancer cells. 5-(hydroxymethyl)-2-Pyrrolidinone is also available with specified stereochemistry (P997525, H948310).

Synthesis

Methyl 5-oxopyrrolidine-2-carboxylate (9 g, 62.93 mmol) was dissolved in methanol (150 mL) under argon protection, stirred and cooled to 0 °C. Subsequently, sodium borohydride (3.6 g, 95.2 mmol) was slowly added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of raw materials, the reaction mixture was quenched with concentrated hydrochloric acid at 0°C. The reaction mixture was filtered and the solid was washed with methanol (2 x 50 mL). The filtrates were combined and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography with 10% methanol/dichloromethane as eluent to give 5-(hydroxymethyl)pyrrolidin-2-one (6 g, 83% yield) as a colorless oil. Liquid chromatography-mass spectrometry (LCMS) analysis showed that the [M+1]+ was 116; chromatographic conditions: X-Select CSH C-18 column (50×3.0 mm, 3.5 μm); mobile phase: 5 mM aqueous ammonium acetate/acetonitrile; flow rate: 0.80 mL/min; retention time (RT): 0.44 min. Thin-layer chromatography (TLC) analysis showed that the unfolding agent was 10% methanol/dichloromethane and the Rf value was 0.3.

References

[1] Patent: WO2015/109109, 2015, A1. Location in patent: Paragraph 1239
[2] Patent: US2017/44182, 2017, A1. Location in patent: Paragraph 1804