Trimethyl borate → Boronic acid, B-(3-propylphenyl)-

Temperature

-78 °C

To a solution of Intermediate 214.1 (130 mg, 0.65 mmol) in 4 mL THF at −78° C., was added BuLi (1.4 M in hexanes, 0.557 mL, 0.78 mmol). The mixture was stirred 5 min at −78° C., then trimethylborate (0.109 mL, 0.975 mmol) was added. The reaction was stirred at −78° C. for 10 min, then was removed from the cooling bath and stirred 1 h. The reaction was quenched with 1 N HCl, then was diluted with EtOAc. The organic phase was washed with 1N HCl and brine, dried (Na2SO4) and concentrated to afford 83 mg of Intermediate 214.2 as a colorless oil, which was used without further purification in the following step.

1. stirringThe reaction was stirred at −78° C. for 10 min
2. customwas removed from the cooling bath
3. stirringstirred 1 h
4. customThe reaction was quenched with 1 N HCl
5. additionwas diluted with EtOAc
6. washThe organic phase was washed with 1N HCl and brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-fe30481f16584759b1c978726444b6d0

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576098B2