[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18]O)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Br:27]P(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][Br:27])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]To a solution of 0.380 mmol of tert-butyl-7-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2.5 ml CH2Cl2 were added at 0° C. 1.139 mmol Et3N and 0.456 mmol tribromophosphine. The mixture was allowed to warm to room temperature and stirred for 1 h. To the reaction mixture were added saturated NaHCO3 solution and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed, dried over MgSO4 and filtered. Evaporation of the solvent gave 105 mg of crude material that was purified by flash chromatography to yield 76 mg of colorless oil (61.3%).
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