Hexane → HCID 13552982, compound

Temperature

-10 °C

To a solution of Compound 3b (0.5 mmol) in tetrahydrofuran (2 mL) at -78° C. under nitrogen was added n-butyllithium in hexane (0.5 mmol). After 30 minutes, a solution of N- formylpiperidine (0.55 mmol) in tetrahydrofuran (0.5 mL) was added dropwise at -78° C. The reaction mixture was stirred for 5 hours while allowing it to warm to -10° C. The reaction was quenched with saturated aqueous ammonium chloride (1 mL) and diluted with diethyl ether (10 mL). The aqueous phase was extracted with diethyl ether (2×10 mL) and the combined organic phases were washed with saturated aqueous ammonium chloride (3×5 mL) and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with ethyl acetate:hexane (2:98) to afford Compound 3c as an oil (Rf =0.2).

1. customThe reaction was quenched with saturated aqueous ammonium chloride (1 mL)
2. additiondiluted with diethyl ether (10 mL)
3. extractionThe aqueous phase was extracted with diethyl ether (2×10 mL)
4. washthe combined organic phases were washed with saturated aqueous ammonium chloride (3×5 mL) and brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was removed in vacuo
7. customthe residue purified by flash chromatography on silica gel
8. washeluted with ethyl acetate:hexane (2:98)

ORD record

ord-8a8d3e9ea0a64d75987f3fbe82dd8e9a

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599341