Diphenylsilane → 1-(Phenylmethyl)pyrrolidine

Temperature

-78 °C

Titanocene dichloride (0.28 g, 1.1 mmol) was dissolved in (15 mL) of tetrahydrofuran in a nitrogen atmosphere, and the reaction mixture was cooled to -78° C., and 2.4 mL of a 1.6M solution of n-butyl lithium in hexane was added. The reaction mixture was stirred for 15 min and then 4.5 mL diphenylsilane (24 mmol) was added. After warming the reaction mixture to room temperature, 1.8 g of N-benzylpyrrolidinone (11 mmol) was added to the black solution, which began bubbling and became warm (i.e., about 30° C.) after 1-2 min. The reaction mixture was stirred overnight at room temperature and then heated to 55° C. for 1 hour. The solution was then poured into 50 mL of ethyl ether and extracted with 1 M HCl (3×50 mL). The aqueous layer was washed with ether (2×25 mL) and then neutralized with a 5 M NaOH solution so that the aqueous layer was basic to pH paper. The product was extracted into ether (3×50 mL) and the emulsion that formed was also extracted with ether (50 mL). The combined ether extracts were dried over MgSO4, filtered, and concentrated in vacuo. N-benzylpyrrolidine was isolated as a yellow oil (1.58 g of 95% pure material, 84% yield).

1. temperatureAfter warming the reaction mixture to room temperature
2. custombegan bubbling
3. temperaturebecame warm (i.e., about 30° C.) after 1-2 min
4. stirringThe reaction mixture was stirred overnight at room temperature
5. temperatureheated to 55° C. for 1 hour
6. additionThe solution was then poured into 50 mL of ethyl ether
7. extractionextracted with 1 M HCl (3×50 mL)
8. washThe aqueous layer was washed with ether (2×25 mL)
9. extractionThe product was extracted into ether (3×50 mL)
10. customthe emulsion that formed
11. extractionwas also extracted with ether (50 mL)
12. dry with materialThe combined ether extracts were dried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo

ORD record

ord-24fcd79f38a749a9ba49881dfe03955f

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05286878