Sodium borohydride → 6-(5-Hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile
Reaktionsgleichung
[CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:4]=1[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:4]=1[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1Komponenten
4
Versuchsvorschrift
A suspension of 6-(5-formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile (0.77 g, 2.5 mmol) in methanol (20 mL) was cooled in an ice bath and treated with sodium borohydride (0.29 g, 7.7 mmol). The reaction mixture was allowed to reach room temperature and was stirred for 72 h. Additional sodium borohydride (0.29 g, 7.7 mmol) was added and stirring at room temperature was continued for 3 h. After quenching with methanol all volatile components were evaporated. The residue was partitioned (ethyl acetate/brine). The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound (0.73 g, 94%) as a brown solid. MS: m/e=309.2 [M+H]+.