Tetrahydrofuran → 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)propan-1-ol

반응식

C[O:2][C:3](=O)[CH:4]([N:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:8]([I:15])=[CH:7]1)[CH3:5].[BH4-].[Li+].C1COCC1>CCO>[I:15][C:8]1[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[N:6]([CH:4]([CH3:5])[CH2:3][OH:2])[CH:7]=1

참가 물질

실험 절차

To a solution of 2-(3-iodo-pyrrolo[3,2-c]pyridine-1-yl)-propionic acid methyl ester (Preparation 57, 18.1 g, 54.8 mmol) in EtOH (300 mL) was added 2M lithium borohydride solution in THF (63.1 mL, 126 mol) at 0° C. The reaction was stirred at this temperature for 30 minutes before warming to room temperature for 18 hours. The reaction was quenched by the addition of water (300 mL) at 0° C. with stirring for 1 hour. The EtOH was removed in vacuo and the resulting residue diluted further with water (600 mL) followed by extraction into 5% MeOH in DCM (250 mL). The organic layer was collected, dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-5% MeOH in DCM to afford the title compound (12 g, 73%).