1-Benzyl-3-pyrrolidinone Chemical Properties

Boiling point:

77 °C/0.01 mmHg (lit.)

Density 

1.091 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.539(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Crystalline Powder, Crystals or Chunks

pka

5.56±0.20(Predicted)

color 

White to off-white

BRN 

1526217

InChI

InChI=1S/C11H13NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5H,6-9H2

InChIKey

DHGMDHQNUNRMIN-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(=O)C1

CAS DataBase Reference

775-16-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-24/25-36

WGK Germany 

3

F 

10

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:1-(Phenylmethyl)-3-pyrrolidinone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-Benzyl-3-pyrrolidinone Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

Substrate used to prepare chiral, alkenyl sulfoximines leading to highly functionalized diazabicycles.1

Uses

1-Benzyl-3-pyrrolidinone is a substrate used to prepare chiral, alkenyl sulfoximines leading to highly functionalized diazabicycles.

Uses

1-Benzyl-3-pyrrolidinone was used as starting reagent in the synthesis of vinyl triflate. It was used to prepare chiral, alkenyl sulfoximines leading to highly functionalized diazabicycles.

General Description

The equilibrium constant for the ketoreductase-catalyzed reduction reaction of 1-benzyl-3-pyrrolidinone has been measured in n-hexane. 1-Benzyl-3-pyrrolidinone on enzymatic asymmetric reduction yields enantiopure 1-benzyl-3-hydroxypyrrolidine, well known intermediate for various drugs.

Synthesis

General procedure for the synthesis of 1-benzyl-3-pyrrolidinone from N-benzyl-3-hydroxypyrrolidine: 12.50 g of oxalyl chloride was slowly added dropwise to 70 mL of dichloromethane, stirred and cooled to -65 °C or lower. Subsequently, a dichloromethane solution of 5.0 g of DMSO was added dropwise, keeping the reaction temperature at -65°C. After dropwise addition, stirring was continued for 30 minutes. Next, 8.80 g of a dichloromethane solution of 1-benzyl-3-hydroxypyrrolidine was added dropwise, maintaining the temperature at -65 °C, and the reaction progress was monitored by TLC. After 2 hours of reaction, triethylamine was slowly added dropwise at -65 °C, controlling the temperature at -65 °C, and stirring was continued for 30 minutes after completion of the dropwise addition. Subsequently, the temperature of the reaction system was raised to 0 °C and water was added dropwise to transform the suspension into a clarified solution. The organic layer was separated, washed with brine and dried to give 8.00 g of 1-benzyl-3-pyrrolidone in 90.90% yield and 95% HPLC purity.

References

[1] Patent: CN106938980, 2017, A. Location in patent: Paragraph 0026-0031
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2465 - 2469

1-Benzyl-3-pyrrolidinone(775-16-6)Related Product Information

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