[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([C:23](OCC)=[O:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C(=O)(O)[O-].[Na+]>C1COCC1>[OH:24][CH2:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[S:15][C:16]=2[CH:22]=1The ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate (1.1 g) was dissolved in dry THF (50 mL) and lithium borohydride (67 mg) was added. The resulting mixture was stirred overnight at room temperature, then heated to reflux for 24 hours. Saturated aqueous sodium bicarbonate was added and the resulting mixture was extracted with ethyl acetate. The resulting solution was concentrated to yield tert-butyl 4-(6-(hydroxymethyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate as a white solid (1.0 g). MS: 350.3 (M+H).
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