Ammonia → HCID 72238032, compound

Participants

Reaction Conditions

Reaction Steps

4.2 g of bicyclo[3.3.1]nonan-2,6-dione-monoethylene ketal (97) were dissolved in 54 mL of 2M ammonia in ethanol and 12.6 mL of titanium(IV) isopropoxide were added. The mixture is stirred at 60° C. overnight. Heating was continued until no further conversion was observed, another 22 mL of ammonia in ethanol was added portionwise over the course of the reaction. The mixture was cooled to room temperature and 1.21 g of sodium borohydride were added portionwise. The mixture was stirred for 2 h and then poured into 100 mL of 2M aqueous ammonia. The formed precipitate was filtered over celite and washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate, the combined organic layer was dried over sodium sulfate and evaporated to dryness. The crude product was taken up in water and lyophilized to give 1.97 g of the desired product. Rt=0.52 min (Method C). Detected mass: 198.3 (M+H+).

Provenance & Evidence