Ammonia → HCID 72238032, compound

Temperature

60 °C

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+).

1. temperatureHeating
2. temperatureThe mixture was cooled to room temperature
3. stirringThe mixture was stirred for 2 h
4. filtrationThe formed precipitate was filtered over celite
5. washwashed with ethyl acetate
6. extractionThe aqueous layer was extracted with ethyl acetate
7. dry with materialthe combined organic layer was dried over sodium sulfate
8. customevaporated to dryness

ORD record

ord-bf3a78b939be4fdfb48b866e1d4eb9bd

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710077B2