Hydrochloric Acid → Ethyl (+/-)-10,11-dihydro-3-methoxy-2-methyl-5H-dibenzo[a,d]cycloheptene-10-acetate

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A mixture of ethyl (±)-10,11-dihydro-2-formyl-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate (220 mg, 0.65 mmol), 10% Pd/C (90 mg), glacial HOAc (15 mL), and conc HCl (2 mL) was shaken at RT under hydrogen (60 psi). After 20 hr, the mixture was filtered through celite®, and the filtrate was concentrated to afford the title compound (200 mg, 95%) as a colorless oil: MS (ES) m/e 325.2 (M+H)+.

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