Tetrabutylammonium Fluoride → HCID 56619794, compound

To a stirred and ice-cold solution of 3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-1-vinylpyrrolidin-2-one (TBSE-VP) (269 mg; 1.0 mmol) in dry tetrahydrofuran (10 mL) was dropwise added a 1.0 m solution of tetrabutylammonium fluoride (2.0 mL; 2.0 mmol; 2.0 equiv.) under an argon atmosphere. Upon completion of the addition the reaction mixture was left stirring at 0° C. for 5 min, allowed to warm to ambient temperature over 5 min and left stirring for another 40 min. The reaction mixture was partitioned between water (5 mL) and ethyl acetate (10 mL) and the aqueous phase was extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Column chromatography (ethyl acetate) afforded the target compound (135 mg; 0.87 mmol; 87%) as a pale yellow liquid.

1. additionUpon completion of the addition the reaction mixture
2. waitwas left
3. stirringstirring at 0° C. for 5 min
4. waitleft
5. stirringstirring for another 40 min
6. customThe reaction mixture was partitioned between water (5 mL) and ethyl acetate (10 mL)
7. extractionthe aqueous phase was extracted with ethyl acetate (3×5 mL)
8. dry with materialThe combined organic extracts were dried over MgSO4
9. concentrationconcentrated under reduced pressure
10. customColumn chromatography (ethyl acetate) afforded the target compound (135 mg; 0.87 mmol; 87%) as a pale yellow liquid

ORD record

ord-e306628a079a4f4f8f43a05893b7fcdf

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006305B2