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

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Reaction Steps

To a stirred solution of methyl1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylate(1.2 g, 4.85 mmol) in MeOH (5 ml) was added 1 N 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 1 N 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) δ 1.47 (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