Sodium Hydroxide → 1-Boc-pyrrolidine-3-acetic acid

Participants

Reaction Steps

To a solution of 6.6 g (27.13 mmol ) of tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate in methanol (150 mL) was added 25 mL (50 mmol) of 2N aqueous NaOH dropwise and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was acidified with 2N hydrochloric acid at 0° C. The organics were extracted with ethyl acetate (×3), washed with brine, dried over anhydrous Na2SO4, and filtered. Evaporation of the solvent gave 5.67 g of [1-(tert-butoxycarbonyl)-pyrrolidin-3-yl]acetic acid. The acid (5.64 g, 24.6 mmol) was converted to the title compound (4.2 g) in 3 steps using the procedure outlined in Example 6. 1H NMR (500 MHz, CDCl3) δ 3.64–3.53 (m, 3H), 3.32 (m, 1H), 3.20 (m, 1H), 2.59 (m, 1H), 2.21 (m, 1H), 1.81 (m 1H), 1.49 (s, 9H).

Provenance & Evidence