(S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamate → (S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

Participants

Reaction Steps

To (S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamate (2.94 mmol, 1.34 g) in Ethanol (35.4 mL) was added palladium hydroxide (2.51 mmol, 0.353 g). The reaction was placed under 2 bar of hydrogen gas and allowed to stir at room temp for 30 mins. The reaction mix was filtered through a dicalite cartridge before washing with EtOH. The solvent was removed before purifying further by SCX (20 g cartridge, 1:1 MeOH/DCM wash, 2M NH3 MeOH elution). The solvent was removed to give the product as a clear gum (810 mg, 86%). MS (ESI): m/z [M+H]+ 322.2

Provenance & Evidence