Hexane → HCID 86730723, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium (1.6 M in n-hexane, 4.72 mL, 7.55 mmol, 1.5 eq) is added dropwise at 0° C. to a stirred solution of (3-chloro-5-fluoro-6-methoxy-quinolin-4-ylmethyl)-phosphonic acid diethyl ester (1.82 g, 5.03 mmol, 1.0 eq) in tetrahydrofuran (130 mL). After 2 hours stirring at 0° C., a solution of (3R,6S)-[6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (1.22 g, 5.03 mmol, 1.0 eq) in tetrahydrofuran (30 mL) is added dropwise within 2 minutes. After 10 minutes stirring at 0° C., the reaction mixture is quenched with water (10 mL). Then solvent is evaporated and the residue is extracted with ethyl acetate (3×150 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 10:1 to 1:1, v/v) to afford (3R,6S)-{6-[3-(3-chloro-5-fluoro-6-methoxy-quinolin-4-yl)-allyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester as a light red solid (1.82 g, 80% yield).

Provenance & Evidence