[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1Into a 250 mL round bottom flask was placed a solution of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-1-carboxylate (15 g, 44.26 mmol) and Pd/C (2.3 g) in CH3OH (absolute) (100 mL). Hydrogen gas was bubbled. The resulting solution was allowed to react, with stirring, for 2 hours while the temperature was maintained at room temperature. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 5.6 g (67%) of 3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine as a yellow liquid.
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