Sodium Hydroxide → 1-(Tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

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Reaction Steps

To a stirred solution of methyl-1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylate (1.2 g, 4.85 mmol) in MeOH (5 ml) was added 1N NaOH (5 ml) and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo, water was added thereto, and neutralized with 1N HCl. The mixture was extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, quant) as a colorless oil. 1H-NMR (CDCl3) δ1.47 (br s, 9H), 2.78-2.83 (br s, 3H), 4.37 (s, 2H), 6.73-6.76 (m, 3H), 7.17 (m, 1H).

Provenance & Evidence