Sodium Hydroxide → 1-tert-Butyl 2-methyl (2R,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate

Participants

Reaction Steps

To a solution of (2R,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine (2.08 g: 7.6 mmole) in methanol (21.0 ml), aqueous 1N-sodium hydroxide (7.6 ml) is added under ice cooling. The mixture is stirred at the same temperature for 25 minutes to give (2R,4S)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine (1.86 g). Yield: 100%. Colorless oil. NMR δ(CDCl3) ppm: 1.44(d, J=9.2 Hz, 9H), 1.9 to 2.4(m, 2H), 3.4 to 3.7(m, 2H), 3.74 (s, 3H), 4.3 to 4.6(m, 2H).

Provenance & Evidence