Benzoyl chloride → HCID 58507543, compound

Temperature

-78 °C

To a stirred solution of 1-(t-butoxycarbonyl)-2-pyrrolidinone (11.9 g, 64.3 mmol) in dry THF (190 mL) at −78° C. was added a solution of LiHMDS (1.0M in toluene, 135 mL, 135 mmol). After stirring at −78° C. for 2 hours, benzoyl chloride (7.5 mL, 64.3 mmol) was added dropwise over 5 minutes while keeping the temperature below −50° C. The mixture was stirred at −78° C. for 4 hours, and the reaction was then quenched with a saturated aqueous NH4Cl solution (200 mL). The mixture was diluted with EtOAc (300 mL) and the organic layer was washed with saturated NaHCO3 (200 mL×2) and saturated aqueous NaCl (200 mL). The organic layer was dried over MgSO4, filtered and concentrated, and the crude product was purified by flash column chromatography (20-60% EtOAc in hexanes) to afford the title compound (14.5 g) as a yellow oil.

1. customthe temperature below −50° C
2. stirringThe mixture was stirred at −78° C. for 4 hours
3. customthe reaction was then quenched with a saturated aqueous NH4Cl solution (200 mL)
4. additionThe mixture was diluted with EtOAc (300 mL)
5. washthe organic layer was washed with saturated NaHCO3 (200 mL×2) and saturated aqueous NaCl (200 mL)
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customthe crude product was purified by flash column chromatography (20-60% EtOAc in hexanes)

ORD record

ord-65bd80e7675245f181c298f5b4cfe022

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242164B2