5-Hydroxymethylpyrrolidin-2-one Chemical Properties

Melting point:

83-85 °C(lit.)

Boiling point:

147-149 °C0.06 mm Hg(lit.)

Density 

1.1808 (rough estimate)

refractive index 

-31 ° (C=5, EtOH)

Flash point:

147-149°C/0.06m

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Dimethylformamide, Water

form 

Crystalline Powder or Flakes

pka

14.35±0.10(Predicted)

color 

White to yellow

optical activity

[α]20/D 31°, c = 5 in ethanol

BRN 

5728422

CAS DataBase Reference

66673-40-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10

HS Code 

29337900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Hydroxymethylpyrrolidin-2-one Usage And Synthesis

Chemical Properties

(R)-5-(Hydroxymethyl)-2-pyrrolidinone is White Powder

Uses

(R)-5-(Hydroxymethyl)-2-pyrrolidinone is a 2-pyrrolidone derivative for therapeutic use as prostanoid receptor agonist.

Uses

Serves as a building block in the synthesis of diphthamide.

Synthesis

Scheme 1, Step B: Preparation of (R)-(-)-5-(hydroxymethyl)-2-pyrrolidinone (3) To a solution of methanol (100 mL) containing methyl (R)-5-oxopyrrolidine-2-carboxylate (Intermediate 2, 13.2 g), sodium borohydride (10.5 g, 278 mmol) was added in batches at 0 °C. The reaction mixture was stirred continuously at 0 °C until the reaction was complete, followed by the addition of acetic acid (3 mL) to quench the reaction. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography using methanol-chloroform (1:9, v/v) as eluent to afford the target product (12.9 g, 97% yield) as a colorless solid. Thin-layer chromatography (TLC) showed an Rf value of 0.33 (unfolding agent system: methanol-chloroform, 1:9, v/v); nuclear magnetic resonance hydrogen spectrum (1H-NMR, CDCl3) δ: 7.17 (s, 1H), 3.92 (s, 1H), 3.85-3.75 (m, 1H), 3.64-3.40 (m, 2H), 2.42-2.35 (m. 2H), 2.2-2.05 (m, 1H), 1.88-1.7 (m, 1H).

References

[1] Patent: WO2014/15246, 2014, A1. Location in patent: Paragraph 0447-0448
[2] Patent: WO2014/144610, 2014, A1. Location in patent: Paragraph 0368; 0377; 0378
[3] Patent: WO2015/9991, 2015, A2. Location in patent: Paragraph 0555-0556
[4] Patent: US2016/60216, 2016, A1. Location in patent: Paragraph 0371-0372
[5] Patent: KR2015/130326, 2015, A. Location in patent: Page/Page column 0409-0411

5-Hydroxymethylpyrrolidin-2-one(66673-40-3)Related Product Information

• 5-Hydroxymethylpyrrolidin-2-one
• 2-Pyrrolidone-5-carboxylic acid sodium salt
• Ethyl L-pyroglutamate
• DIRHODIUM (II) TETRAKIS(METHYL 2-PYRROLIDONE-5(R)-CARBOXYLATE)ACETONITRILE/2-PROPANOL COMPLEX
• Cyclopentene oxide
• L-PYROGLUTAMIC ACID PENTACHLOROPHENYL ESTER
• CLASTO-LACTACYSTIN
• EQUISETIN
• Ethyl D-(-)-pyroglutamate
• DL-Pyroglutamic acid
• D-Pyroglutamic acid
• L-Arginine-L-pyroglutamate
• Z-PYR-OH
• Z-D-PYR-OH
• CALCIUM PIDOLATE
• (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate
• L-Pyroglutaminol
• ALPHA-PYRIDOIN