1-(Bromomethyl)-2-phenylbenzene → 1-[1,1'-Biphenyl]-2-yl-6,6,6-trifluoro-2-[4-(phenylmethyl)morpholin-2-yl]hexan-2-ol

Participants

Reaction Steps

Compound 67 is prepared from 10 (0.853 g, 2.71 mmol) and 2-phenyl benzyl magnesium bromide (0.25 M solution in diethyl ether, 1.2 eq) following General Procedure 2. 2-Phenylbenzyl magnesium bromide is prepared from commercially available (Aldrich) 2-phenylbenzyl bromide following General Procedure 5. Further 2-phenyl benzyl magnesium bromide is added later (19.2 mL, 4.8 mmol). Purification by automated column chromatography (eluent, EtOAc/cyclohexane 20/80 to 40/60 [v/v]), followed by ion exchange chromatography gives 67 as a viscous oil (369 mg, 28%). MW 483.58; C29H32F3NO2; LCMS: (6 min method) m/z 484 [M+H]+, RT 4.26 min.

Provenance & Evidence