C([N:14]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[C:18]1([CH:16]2[CH2:17][NH:14][CH2:15]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Add 20% palladium hydroxide on activated carbon (0.130 g) and ethanol (25 mL) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the mixture at RT for 15 min. Vent the hydrogen from the reaction vessel and purge the reaction vessel with nitrogen. Add 1-benzhydryl-3-phenylazetidine (0.515 g, 0.00172 mol) and ethanol (75 mL) to the pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the reaction at RT for 20 h. Turn off the agitation, vent the excess hydrogen from the vessel, purge the vessel with nitrogen and filter the reaction mixture to remove the palladium on carbon catalyst. Concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM) to give the title compound (76 mg, 34%).
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