Methanol → HCID 12073627, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring mixture consisting of (Z)-isopropyl 7-((1R,2R,3S,5S)-2-((E)-3-(benzo[b]thiophen-2-yl)-3-oxoprop-1-enyl)-3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step H, 13.4 g) in methanol (325 mL) cooled to −40° C. was added CeCl3 heptahydrate (9.46 g). The reaction mixture was further cooled to −78° C. and was stirred for an additional hour. Sodium borohydride (1.89 g) was added and the reaction mixture was stirred for one hour at −78° C. Upon completion (as visualized by TLC), the reaction was quenched by the addition of acetone and the mixture was warmed to room temperature. The mixture was subsequently acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude title intermediate (15.2 g). The crude intermediate was carried on with no further purification.

Provenance & Evidence