[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][CH:2]1[C:10](OC)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1.O.C(OCC)(=O)C>[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][CH:2]1[CH2:10][OH:11]Reaction under a nitrogen atmosphere. A solution of intermediate (4) (0.042 mol) in THF (48 ml) was added dropwise to LiAlH4 (1 Min THF) (0.0466 mol) and cooled with an ice-water bath. The resulting reaction mixture was stirred for one hour at room temperature. The reaction mixture was treated carefully with a 10% NH4Cl solution and it was diluted with water and ethyl acetate. The reaction mixture was filtered over Celite and the filtrate was extracted. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was washed with DCM, filtered off and dried, yielding 2.78 g of (±)-1,3-dioxolo[4,5-b]pyridine-2-methanol (intermediate 5).
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