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

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).

1. customTo nitrogen flushed pressure bottle
2. additionwas added Pd/c (200 mg) under nitrogen
3. customwas hydrogenated at 50 psi overnight
4. washwashed with MeOH
5. concentrationThe filtrate was concentrated
6. customthe residue was used for the next step without purification

ORD record

ord-ff5c39aa38a44162947c42f1d3de5700

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415340B2