1,4-Bis(dihydroquinidine)phthalazine → HCID 66835389, compound

Participants

Reaction Steps

AD-mix. Alcohol 12Z (0.0138 g, 0.0325 mmol, 1.0 equiv) was dissolved in t-BuOH (0.33 mL) and water (0.33 mL). To this solution AD-mix-α (0.091 g, 2.8 g/mmol) was added followed by methanesulfonamide (0.0062 g, 0.065 mmol, 2.0 equiv). This solution was allowed to stir for 6 h at 25° C. Upon completion, an aqueous solution of sodium sulfite (5 mL) was added, and the quenched reaction mixture was allowed to stir for 1 h. The mixture was then diluted with ethyl acetate (5 mL), the phases separated, and the aqueous layer was then washed with ethyl acetate (4×5 mL). The combined organic layers were then washed with a saturated brine solution (20 mL), dried over MgSO4, vacuum filtered through a pad of Celite, and the resulting filtrate was evaporated to dryness using a rotary evaporator. The solid was then purified using silica gel chromatography (pre-absorbed on silica gel, step gradient of 3:1 hexane/EtOAc followed by 100% MeOH) to afford 1 as a pure white crystalline solid (0.0114 g, 76% yield). The other isomeric triols were made by an analogous procedure to afford 13 (0.0100 g, 56% yield from 12Z with AD-mix-β), 14 (0.0137 g, 64% yield 12Z with AD-mix-α), 15 (0.0169 g, 76% yield from 12E with AD-mix-β).

Provenance & Evidence