Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate → 4-(Dibenzylamino)-2-methylcyclopentanecarboxylic acid

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Reaction Conditions

Reaction Steps

Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate (3.65 g, 10.38 mmol) was dissolved in a mixture of HCl (6 N aqueous, 20 mL) and 1,4-dioxane (50 mL) and the resulting mixture was heated at about 60° C. for about 72 h. The organic solvent was removed under reduced pressure. The aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 (40 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine (40 mL), dried over anhydrous MgSO4 and concd under reduced pressure to yield 4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (3.3 g, 98%) as a white amorphous solid: LC/MS (Table 1, Method a) Rt=1.66 min; MS m/z 324 (M+H)+.

Provenance & Evidence