Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=O)[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[BH4-].[Na+]>CO.[Pd].C(O)C>[NH:2]1[CH2:7][CH2:6][C:5]2([CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1To a stirred solution of the spiro[2H-1-benzopyran-2,4'-piperidin]-4(3H)-one, hydrochloride (53 mg, 0.21 mmol) in methanol (5 mL) at 0° C., was added sodium borohydride (38 mg, 1 mmol) in several portions. After 30 minutes the mixture was evaporated and then treated with concentrated hydrochloric acid (2 mL) for 30 min. Evaporation gave a residue which was hydrogenated with palladium on carbon (10%, 10 mg), H2 (1 atm) in ethanol for two hours. Filtration to remove the catalyst gave the crude intermediate (89 mg) which was used without further purification.
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