Sodium Hydroxide → 1-(Tert-butoxycarbonyl)-4-phenylpiperidine-3-carboxylic acid

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Reaction Steps

To a solution of 89 mg of methyl ester (from Example 104, Step B) in 1.5 mL EtOH was added 1.0 mL of 0.5N NaOH. After 36 h the reaction was concentrated under vacuum. The residue was dissolved in 25 mL H2O and washed with 25 mL Et2O. After separating layers, the aqueous phase was acidified to pH 2 using 0.5N KHSO4. The aqueous phase was extracted with 3×25 mL of CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated under vacuum to give 58 mg of a white foam which was taken on without further purification.

Provenance & Evidence