1-Benzyl-3-pyrrolidinone

Product Name1-Benzyl-3-pyrrolidinone
CAS775-16-6
MFC11H13NO
MW175.23
EINECS212-274-0
MOL File775-16-6.mol

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
pka	5.56±0.20(Predicted)
form	Crystalline Powder, Crystals or Chunks
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
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

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

Usage And Synthesis

Chemical Properties

clear yellow liquid

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.

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.

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

775-15-5

775-16-6

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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