Boron trifluoride etherate → HCID 86725309, compound

Temperature

0 °C

The product from step (a) was dissolved in DCM (20 ml) and cooled to 0° C. To the stirred solution triethylsilane (943 μL, 5.85 mmol) was added, followed by borontrifluoride etherate (456 μL, 3.66 mmol). After 1 hour, additional borontrifluoride etherate (456 μL, 3.66 mmol) was added and the reaction mixture was stirred for an additional hour at 0° C. The reaction was quenched with saturated aqueous NaHCO3 (50 ml) and the aqueous layer was extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo. The residue was purified by silica gel chromatography (gradient elution: 0 to 20% EtOAc in hexane) to give the sub-title compound as a colorless oil (103 mg). 1H NMR (CDCl3) δ 7.01-6.93 (m, 2H); 4.16 (q, J=7.2 Hz, 2H); 3.75-3.68 (m, 2H); 3.52-3.43 (m, 2H); 3.11-2.99 (m, 4H); 2.80-2.72 (m, 2H); 2.25-2.14 (m, 1H); 2.06-1.99 (m, 1H); 1.29 (t, J=6.9 Hz, 3H); 0.88-0.77 (m, 1H); 0.55-0.41 (m, 2H); 0.34-0.26 (m, 1H); 0.20-0.13 (m, 1H); MS: ESI (positive): 300, (M+1).

1. customThe reaction was quenched with saturated aqueous NaHCO3 (50 ml)
2. extractionthe aqueous layer was extracted with DCM (3×)
3. washThe combined DCM extracts were washed with brine
4. dry with materialdried over Na2SO4, and solvent
5. customevaporated in vacuo
6. customThe residue was purified by silica gel chromatography (gradient elution: 0 to 20% EtOAc in hexane)

ORD record

ord-776180d097574d15814e8f9edc044699

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284277B2