Hydrochloric Acid → 3-Hydroxymethyl-3,4-dihydro-2H-naphtho[1,8-cd]azepin-1-one

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Reaction Steps

To a solution of 1-oxo-1,2,3,4-tetrahydronaphtho[1,8-cd]azepine-3-carboxylic acid methyl ester (70 mg, 0.28 mmol) in MeOH (5 mL) is added LiBH4 (18.3 mg, 0.83 mmol) and the mixture is stirred at RT for 1 h. Ethyl acetate is added followed by ice and 1N HCl. The mixture is washed with brine then water and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by preparative HPLC to give the title compound.

Provenance & Evidence