Ethyl Acetate → HCID 86749596, compound

Participants

Reaction Steps

A mixture of trans-2-benzoyl-6-hydroxy-6-(4'-t-butyldimethylsilyloxyphenyl)decahydroisoquinoline (Example 48, 740 mg, 1.61 mmol) and lithium aluminum hydride (0.31 g, 8 mmol) in anhydrous THF (20 mL) was stirred at reflux temperature under a nitrogen atmosphere for 19.5 h. The reaction mixture was cooled to room temperature and quenched with excess ethyl acetate, followed by water (0.3 mL), a 1N NaOH solution (0.3 mL) and water (1 mL). The precipitate was filtered through celite; the filtrate was dried over magnesium sulfate and filtered. Removal of solvent in vacuo gave an oil. Column chromatography (ethyl acetate) gave the product, a solid (209 mg): mp 108°-109° C., NMR (CDCl3, 200 MHz): 7.4-7.2 (m, 7H), 6.8 (d, 2H, J=7), 3.55 (s, 2H), 2.95 (br d, 1H, J=8), 2.85 (br d, 1H, J=8), 2.2 (s, 2H), 2.1-1.2 (m, 11H); Anal. Calcd for C22H27NO2.O.3H2O: C, 77.06, H, 8.11, N, 4.09; Found C, 76.82, 76.83, H, 7.95, 8.15, N, 3.88, 3.80.

Provenance & Evidence