[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:4][CH2:3]1A solution of 471 mg (2.0 mmol) of 4,4-dimethyl-1-phenyl-3,4-dihydroisoquinoline in MeOH (6 ml) was cooled to 0° C. and 151 mg (4.0 mmol) of NaBH4 were added in portions. After stirring for 3 h at RT a saturated aqueous NH4Cl solution was added. Then most of the methanol was removed under vacuum and the residue was extracted with EE. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 19 mg (0.08 mmol, 4%) of 4,4-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline were obtained as the residue, which was reacted further with no additional purification.
Loading…
