[CH:1]([C:3]1[S:11][C:10]2[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=2[CH:4]=1)=O.[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:19]1([CH2:1][C:3]2[S:11][C:10]3[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=3[CH:4]=2)[CH2:22][CH2:21][CH2:20]1tert-Butyl 2-formyl-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (0.3 g, 0.122 mmol) and azetidine (96 mg, 1.683 mmol) were dissolved in 1,2-dichloro-ethane (7 ml) and stirred at room temperature for 10 min. Sodium triacetoxyboro-hydride (0.331 g, 1.571 mmol) was added and the resulting mixture stirred at room temperature for 48 h. Saturated sodium hydrogen carbonate solution was added and the phases were separated. The aqueous phase was extracted with diethylether (3×) and the organics were washed with saturated sodium chloride solution (1×). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate/methanol, 10:1). Yield: 0.28 g (81%).
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