Hydrochloric Acid → HCID 69890313, compound

Participants

Reaction Steps

(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%).

Provenance & Evidence