[Li]CCCC.[Si:6]([O:13][CH2:14][C:15]1[N:16]=[N:17][N:18]([CH3:20])[CH:19]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].CN([CH:24]=[O:25])C.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.CO>[CH3:10][C:9]([Si:6]([CH3:7])([CH3:8])[O:13][CH2:14][C:15]1[N:16]=[N:17][N:18]([CH3:20])[C:19]=1[CH2:24][OH:25])([CH3:12])[CH3:11]A solution of BuLi (23.6 mmol) in hexanes (1.6 M, 14.7 ml) was added to a stirred solution of 4-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-[1,2,3]triazole (3.00 g, 13.2 mmol) in THF (50 ml) at −78° C. under N2. The resulting solution was stirred at −78° C. for 15 min, then warmed to −40° C. and recooled to −78° C. DMF (4.97 ml, 64.2 mmol) was added and the reaction was allowed to warm to room temperature. MeOH (50 ml) was added, followed by sodium borohydride (1.21 g, 32.1 mmol) and the reaction mixture was stirred at room temperature for 30 min. NH4Cl solution (50 ml) was added cautiously. The organic solvents were removed under reduced pressure, then 4N NaOH solution (50 ml) was added and the organics were extracted with CH2Cl2 (3×100 ml). The combined organic extracts were washed with NH4Cl solution (50 ml) and brine (50 ml), then dried and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica using 3% MeOH/CH2Cl2 to yield the desired hydroxymethyltriazole (2.83 g, 83%). 1H NMR (360 MHz, CDCl3) δ 4.77 (2H, s), 4.62 (2H, d, J=5.9 Hz), 3.90 (3H, s), 0.78 (9H, s), 0.00 (6H,s). m/z (ES+) 258 (M+H+).
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