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| | 1-Benzyl-3-pyrrolidinone Basic information |
| | 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.) | | Fp | >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) |
| 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 |
| | 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 Preparation Products And Raw materials |
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