Water → HCID 86587361, compound

Participants

Reaction Steps

(3aR,4R,5R,6aS)-5-(1-Ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-ol (XI, EXAMPLE 7) is dissolved in dry THF (10 mL) and added to a mixture containing potassium 5-(triphenylphosphoranylidene)pentaonate (PREPARATION 1) solution at −10° to −5°. The resulting mixture is stirred for about 3 hours at less than −5°. Water (30 mL; 0°) is added over 10 minutes, then ethyl acetate (20 mL) and aqueous THAM solution (10 mL) is added. The phases are separated and the organic phase is washed with aqueous THAM solution (15%, 2×15 mL). The aqueous phases are combined and washed once with ethyl acetate (15 mL). MTBE (50 mL) is added to the combined aqueous phases. The mixture is acidified to pH=3 with aqueous phosphoric acid (40%). The organic phase is separated and concentrated under reduced pressure to 20 mL. Solids (5-diphenypphosphinopentanoic acid) crystallized. MTBE (50 mL) is added and the slurry concentrated under reduced pressure to a volume of 20 mL. The solid is filtered and washed with MTBE (100 mL). The filtrate is concentrated under reduced pressure to give the title compound.

Provenance & Evidence