[CH3:1][N:2]([CH3:11])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1)=[O:4].[CH2:12]=O.[H][H]>C(O)(=O)C.O.[Pt]=O>[CH3:12][N:6]1[CH2:7][C@H:8]([OH:10])[CH2:9][C@H:5]1[C:3]([N:2]([CH3:11])[CH3:1])=[O:4]To a solution of (2S,4R)-2-dimethylaminocarbonyl-4-hydroxypyrrolidine (2.0 g) in acetic acid (14.4 ml) and water (8 ml), 37% aqueous formaldehyde solution (1.27 g) and platinum oxide (38 mg) were added, and the mixture was hydrogenated at room temperature for 7 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent. The residue was dissolved in dichloromethane and dried over magnesium sulfate. Potassium carbonate (3.5 g) was added thereto, and the mixture was stirred for 1.5 hours, followed by filtration. Removal of the solvent gave (2S,4R)-1-methyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine.
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