Borane → HCID 68721715, compound

Temperature

-78 °C

An ambient solution of oxazole (1.00 g, 14.5 mmol) and borane.tetrahydrofuran complex (14.5 mL, 14.5 mmol, 1 M in tetrahydrofuran) was stirred for 30 min. The reaction was cooled to −78° C., and n-butyllithium (9.5 mL, 15.2 mmol, 1.6 M in hexane) was added dropwise. After 30 minutes, cyclopentanone (1.42 mL, 16.0 mmol) was added dropwise. After 30 minutes, the cold (−78° C.) reaction was quenched by the addition of 5% acetic acid in ethanol (70 mL) and warmed to room temperature. The solution was diluted with diethyl ether (10 0 mL) and saturated NaHCO3 (50 mL). Layers were separated, and the organics were washed with brine (1×50 mL), dried over Na2SO4, concentrated, under reduced pressure, and purified by chromatography on SiO2 gel, eluting with 50% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.59-1.71 (m, 2H), 1.72-1.84 (m, 2H), 1.84-1.96 (m, 2H), 1.98-2.09 (m, 2H), 5.40 (s, 1H), 7.11 (s, 1H), 8.02 (s, 1H).

1. waitAfter 30 minutes
2. customthe cold (−78° C.) reaction
3. customwas quenched by the addition of 5% acetic acid in ethanol (70 mL)
4. temperaturewarmed to room temperature
5. additionThe solution was diluted with diethyl ether (10 0 mL) and saturated NaHCO3 (50 mL)
6. customLayers were separated
7. washthe organics were washed with brine (1×50 mL)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated, under reduced pressure
10. custompurified by chromatography on SiO2 gel
11. washeluting with 50% ethyl acetate in hexane

ORD record

ord-1f5ba8d4b9374e8aad3ab18d31804b0d

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242139B2