[N:1]([CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1A 40 ml vial was charged with 5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one (100 mg, 0.43 mmol, INTERMEDIATE 14), palladium on carbon (5 mg), and methanol (15 ml). The reduction was effected using a balloon filled with hydrogen at room temperature overnight. The catalyst was removed through filtration on a pad of Celite pre-rinsed with methanol. The Celite pad was further rinsed with methanol (2×5 ml) and the eluent concentrated in vacuo to provide 75 mg (85%) of the title compound. Mass spectrum (ESI) 207.2 (M+1).
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