Hydrochloric Acid → HCID 69890313, compound

(1R)-2-Carbomethoxy-8-oxabicyclo(3.2.1)octa-2-ene-3-(S)-camphanate, (1R, 1′S)-19 (1.76 g, 4.8 mmol) was dissolved in THF (15 mL) and then methanol (5 mL) and water (5 mL) were added. The resulting solution was cooled in an ice bath and lithium hydroxide (325 mg, 7.7 mmol) was added in one portion. After 20 min no (1R, 1′S)-19 remained. The solution was neutralized with 1 M hydrochloric acid. Ether (200 mL) was then added and the ethereal solution was washed with brine and dried (MgSO4). Evaporation gave 1.38 g of the crude reaction product. This was chromatographed (SiO2, 50 g, eluent: 20% ether in hexanes) to yield 833 mg (94%) of the pure title compound. 1H-NMR and TLC were identical with the racemic ketone 13. Under chiral HPLC conditions (Chiralcel OC column, eluent: 10% isopropanol in hexanes 1 mL/min.) tR (1S)-13=6.99 min (1.78%); tR (1R)-13=10.92 min (98.21%, ee=96.4%).

1. temperatureThe resulting solution was cooled in an ice bath
2. washthe ethereal solution was washed with brine
3. dry with materialdried (MgSO4)
4. customEvaporation
5. customgave 1.38 g of the crude
6. customreaction product
7. customThis was chromatographed (SiO2, 50 g, eluent: 20% ether in hexanes)

ORD record

ord-c1c1be924fa34cdda41f561fc5c1db82

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677338B2