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, 2 H), 1.72-1.84 (m, 2 H), 1.84-1.96 (m, 2 H), 1.98-2.09 (m, 2 H), 5.40 (s, 1 H), 7.11 (s, 1 H), 8.02 (s, 1 H).

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-b985cd58f2214435ac6c0a512a538917

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901152B2