Benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-ylcarbamate → (1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Participants

Reaction Steps

A suspension of palladium hydroxide (0.498 mmol, 350 mg) and benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-ylcarbamate (2.69 mmol, 1.2 g) in ethanol (30 mL) was hydrogenated at 2 bar pressure for 30 min before the reaction vessel was vented and the whole filtered through a pad of dicalite. The pad was washed with EtOAc and the filtrate concentrated under reduced pressure. The residue was purified using SCX eluting with 2N NH3/MeOH to give a clear oil which solidified on standing (700 mg, 2.25 mmol, 83%). 1H NMR (400 MHz, CDCl3) δ 1.65 (m, 1H) 2.51 (m, 1H) 2.80 (m, 1H) 2.95 (m, 1H) 1.35 (t, 1H) 4.60 (s, 2H) 5.26 (s, 2H) 7.12 (d, 2H) 7.30 (d, 1H) 7.42 (s, 1H).

Provenance & Evidence