[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[NH:13][C:12](=O)[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[CH2:9]1.Cl>C1COCC1.[OH-].[Na+].O>[CH3:7][CH:8]1[NH:13][CH2:12][C:11]2[CH:15]=[CH:16][S:17][C:10]=2[CH2:9]1
To a suspension of LAH (0.38 g, 10 mmol) in THF (10 ml) a solution of 6-methyl-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (0.5 g, 3 mmol) in THF (10 ml) was added dropwise. The mixture was stirred for 3 h under reflux and cooled to 0° C. with ice. The solution of 0.4 ml of water in 2 ml THF, 25% NaOH (0.4 ml) and water (1.2 ml) were added carefully step by step. The mixture was stirred for 30 min, filtered and concentrated on rotary evaporator. The residue was purified by flash column chromatography on silica gel (eluent: chloroform/methanol—0→20%) to give yellowish oil. Then, 6 N isopropanolic HCl was added to the oil, stirred for 5 min, concentrated on rotary evaporator, triturated with diethyl ether, filtered, washed with ether and dried in vacuo to give 0.37 g of crystalline compound.
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