(+/-)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole → (+/-)-2-(2,3-dihydro-1H-isoindol-1-yl)-4-fluoro-phenol
Reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[O:24]CC1C=CC=CC=1)C1C=CC=CC=1>CCO.[Pd]>[CH:9]1([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[OH:24])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][NH:8]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution under N2 of (±)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole (181 mg, 0.44 mmol, 1.0 eq.) in EtOH (20 mL), palladium on activated carbon (10 wt. %, 60 mg) was added. The flask was evacuated and backfilled with H2 (3×). The black suspension was stirred at r.t. under an H2-atmosphere for 18 hours. The suspension was filtered through Celite, the Celite rinsed with EtOH. The filtrate was concentrated in vacuo. The residue was filtered and then purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give (±)-2-(2,3-dihydro-1H-isoindol-1-yl)-4-fluoro-phenol.