[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.C(N(CC)CC)C.Br[CH2:25][CH2:26][CH2:27][OH:28].[Na+].[I-]>O1CCCC1.C(OCC)(=O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:10]3)=[CH:7][CH:8]=1
To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (151 mg, prepared following the procedure reported in WO 2005080382) in dry tetrahydrofuran (3.3 mL), triethylamine (0.112 mL), 3-bromo-1-propanol (0.073 mL) and NaI were added and the resulting mixture was heated at reflux for 4 hours. After cooling at room temperature it was diluted with ethyl acetate (20 mL), washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with dichloromethane/methanol from 99/1 to 97/3 to give the title compound as a colourless oil (144 mg).
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