(2S,4S)-1-Benzyl 2-methyl 4-(2,2-difluoroethoxy)pyrrolidine-1,2-dicarboxylate → (2S,4S)-Methyl 4-(2,2-difluoroethoxy)pyrrolidine-2-carboxylate

Participants

Reaction Steps

To nitrogen flushed pressure bottle was added Pd/c (200 mg) under nitrogen. A solution of (2S,4S)-1-benzyl 2-methyl 4-(2,2-difluoroethoxy)pyrrolidine-1,2-dicarboxylate (2.0 g, 5.83 mmol) in MeOH (140 mL) was added to the bottle. The reaction mixture was hydrogenated at 50 psi overnight. The reaction mixture was passed through a pad of celite and washed with MeOH. The filtrate was concentrated and the residue was used for the next step without purification. 1H NMR (CDCl3, 400 MHz) δ ppm 3.56-3.79 (1H, m), 3.96 (1H, br s), 3.60-3.70 (1H, m), 3.62 (3H, s), 3.43-3.50 (2H, m), 3.07-3.09 (1H, m), 2.94-3.03 (1H, m), 2.78-2.87 (1H, m), 2.05-2.15 (2H, m); 13C NMR (126 MHz, CDCl3) δ ppm 174.72 (1C), 114.40 (1C, t, J=241 Hz), 80.41 (1C), 67.96 (1C, t, J=27.6 Hz), 58.78 (1C), 52.40 (1C), 52.29 (1C), 52.19 (1C, s), 35.96 (1C).

Provenance & Evidence