Tetrabutylammonium Fluoride → HCID 118062488, compound

To a solution of Intermediate 302A (1.8 g, 4.94 mmol) in THF (30 mL) was added TBAF (5.93 mL, 5.93 mmol, 1M in THF) at −78° C. and the reaction mixture was stirred at RT for 1 h. It was then quenched with ice-cold water and extracted with ethyl acetate (3×25 mL). The combined organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (4 g REDISEP® column, eluting with 25% ethyl acetate in hexanes). Fractions containing the product were combined and evaporated to afford the Intermediate 302B as a pale yellow liquid (0.8 g, 69%). 1H NMR (400 MHz, chloroform-d) δ ppm 5.06 (s, 1H), 4.51-4.72 (m, 2H), 3.15 (s, 6H), 2.56 (dd, J=13.55, 2.01 Hz, 2H), 2.21 (d, J=14.06 Hz, 2H), 1.26 (d, J=6.02 Hz, 6H).

1. customIt was then quenched with ice-cold water
2. extractionextracted with ethyl acetate (3×25 mL)
3. dry with materialThe combined organic layer was dried over sodium sulfate
4. filtrationfiltered
5. concentrationthe filtrate concentrated
6. customThe crude product was purified by silica gel chromatography (4 g REDISEP® column, eluting with 25% ethyl acetate in hexanes)
7. additionFractions containing the product
8. customevaporated

ORD record

ord-1cd591bd916049278484115bc9dee103

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273058B2