Water → HCID 57941509, compound

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Reaction Steps

A solution of lithium aluminum hydride in tetrahydrofuran (Aldrich; 2 M; 80 μL; 0.16 mmol) was added to a solution of [(4S,7R)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-3-oxo-2,3,4,5,6,7-hexahydro-4,7-methano-indazol-1-yl]-acetic acid ethyl ester (Example 92; 57 mg, 0.15 mmol) in dry tetrahydrofuran (EMScience DriSolve; 700 μL) over 1 min, and the solution was stirred at room temperature for 18 h. Water (4 mL) was added and the mixture was stirred for 10 min. 2M aqueous sodium hydroxide solution (4 mL, 8 mmol) was added and the mixture was stirred for 10 min. The mixture was extracted with dichloromethane (50 mL) and the organic extract was dried (magesium sulfate), filtered, evaporated, and purified using an ISCO 4 g column, eluting with 0-10% methanol/ethyl acetate. Fractions containing the product were combined, evaporated, co-evaporated successively with methanol and ether, and then dried under high vacuum at 75° C. to give (4S,7R)-2-(2,4-difluoro-phenyl)-1-(2-hydroxy-ethyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (8 mg, 16%) as a white solid. ES(+)-MS (M+H) 349.

Provenance & Evidence