Acetonitrile → (8-hydroxy-7-isopropyl-1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)acetonitrile

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (684 mg, 4.24 mmol) in tetrahydrofuran (3 mL) was added 1.6M butyllithium/hexane solution (2.65 mL, 4.24 mmol) at −78° C., and the mixture was stirred for 15 min. A solution of acetonitrile (234 μL, 4.45 mmol) in tetrahydrofuran (1 mL) was added thereto, and the mixture was stirred for 30 min. Then, a solution of 7-isopropyl-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (460 mg, 2.12 mmol) in tetrahydrofuran (6 mL) was added. After stirring for 20 min, the reaction solution was diluted with saturated aqueous ammonium chloride solution, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (457 mg, yield 83%).

1. stirringthe mixture was stirred for 30 min
2. stirringAfter stirring for 20 min
3. customthe solvent was evaporated under reduced pressure
4. additionThe residue was diluted with ethyl acetate
5. washthe mixture was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

ORD record

ord-01616ccdb9d243c291041768aa89a992

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273761B2