Sodium Hydroxide → (r)-1-(4-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid

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Reaction Steps

The above ester (3.5 g, 8.7 mmol) was dissolved in ethanol (40 ml). 5 N Sodium hydroxide (4 ml) was added and the mixture was allowed to stand for 3 days. Ethanol was evaporated in vacuo and the residue was dissolved in water (50 ml). The solution was washed with diethyl ether (30 ml) and acetic acid (3 ml) was added to the aqueous phase which subsequently was extracted with dichloromethane (50 ml). The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The residue was filtered through silica gel (20 g) using ethanol as eluent. The solvent was evaporated and acetone was added to the residue. The solid was isolated by filtration and dried to give 1.8 g (55%) of the title compound.

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