HCID 68830173, compound → HCID 58742377, compound

Temperature

0 °C

A solution of (2R,4aR,10aR)-4a-Ethyl-2,7-dihydroxy-2-pyridin-3-yl-1,4,4a,9,10,10a-hexahydro-2H-phenanthren-3-one (30 mg, 0.09 mmol) in tetrahydrofuran (8 mL) was cooled to 0° C. A 1.0 M solution of methyllithium/lithium iodide complex in tetrahydrofuran (0.43 mL, 0.43 mmol) was added and the mixture was allowed to stir from 0° C. to room temperature over 5 hours. The solution was cooled to 0° C. and additional 1.0 M methyllithium/lithium iodide solution (0.2 mL, 0.2 mmol) was added. After the mixture was allowed to stir overnight at room temperature, it was again cooled to 0° C. and more methyllithium/lithium iodide solution (0.3 mL, 0.3 mmol) was added. After stirring the mixture for a further 4 hours at room temperature, it was quenched with water and saturated aqueous ammonium chloride solution. The mixture was extracted six times with ethyl acetate, and the combined extracts were washed with brine, dried over magnesium sulfate and concentrated. The title compound (2 mg, 6%) was isolated by chromatography on silica gel eluting with a gradient of 2% to 10% methanol in chloroform. Mass spectrum (m/e) 354 (M++1).

1. stirringto stir overnight at room temperature
2. temperatureit was again cooled to 0° C.
3. stirringAfter stirring the mixture for a further 4 hours at room temperature
4. customit was quenched with water and saturated aqueous ammonium chloride solution
5. extractionThe mixture was extracted six times with ethyl acetate
6. washthe combined extracts were washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated

ORD record

ord-bf3a0e156a6c477796adf1551c41a1d4

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138406B2