[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH:20]=[O:21])=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH2:20][OH:21])=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1To a solution of 2-[N-(cyclopentylmethyl)-N-ethylamino]quinoline-3-carbaldehyde (25 mg, 0.088 mmol) in ethanol (1 mL) is added sodium borohydride (5 mg, 0.13 mmol) and the mixture is stirred for 1 hour. After addition of sat. ammonium chloride and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated to give {2-[N-(cyclopentylmethyl)-N-ethylamino]quinolin-3-yl}methanol, which is used without further purification.
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