3,4-dihydro-2H-pyran → HCID 57857047, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-2-((tert-butyldiphenylsilyloxy)methyl)-3-fluoro-5-hydroxycyclopentyl)hept-5-enoate (prepared in Step D, 28.6 g, 52.8 mmol) in anhydrous DCM (500 mL) was added dihydropyran (6.69 g, 79.3 mmol). The reaction mixture was cooled to 0° C. and p-toluenesulfonic acid (25 mg) was subsequently added and the reaction was stirred for 2 hours at 0° C. The reaction mixture was then allowed to warm to room temperature and stirring was continued for another 2 hours. The crude reaction mixture was transferred to a separatory funnel, washed with saturated aqueous sodium bicarbonate solution and then with brine. The organic phase was dried over sodium sulfate, filtered, and the solvents were removed by evaporation to afford the crude title intermediate (32.7 g). The crude intermediate was carried on with no further purification.

Provenance & Evidence