[F:1][C:2]([F:22])([F:21])[S:3]([O:6][C:7]1[C:15]2[N:11]([CH:12]=[CH:13][CH:14]=2)[C:10]([C:16](OCC)=[O:17])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[BH4-].[Na+].O>CO>[F:22][C:2]([F:1])([F:21])[S:3]([O:6][C:7]1[C:15]2[N:11]([CH:12]=[CH:13][CH:14]=2)[C:10]([CH2:16][OH:17])=[CH:9][CH:8]=1)(=[O:4])=[O:5]To a solution of ethyl 8-(((trifluoromethyl)sulfonyl)oxy)indolizine-5-carboxylate (30 g, 89 mmol) in MeOH (300 mL) was added NaBH4 (13.5 g, 0.356 mol) at 0° C. under N2. The reaction mixture was stirred at rt overnight. After the completion, to the reaction was added water, extracted with EtOAc, washed with brine, dried and concentrated to give the desired product 5-(hydroxymethyl)indolizin-8-yl trifluoromethanesulfonate (50 g, crude).
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