反应详情

Palladium hydroxide (20% on carbon, 6.38 mmol, 0.895 g) was wetted in a hydrogenation vessel before addition of (S)-benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-ylcarbamate (6.38 mmol, 2.84 g) and ethanol (50 mL) followed by aqueous 5N HCl solution (5.00 mL). The mixture was stirred under 2 bar of hydrogen for 1 hour before diluting with DCM (100 mL) and filtration through a dicalite pad which was then washed with 10% MeOH/DCM (200 mL). Combined organics were concentrated and partitioned between ethylacetate and saturated sodium carbonate solution. The organic layer was concentrated to give a light yellow oil which was purified on silica eluting with 5.5% 2M NH3-MeOH/DCM to give (S)-(1-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (1.40 g, 70.7%). 1H NMR (400 MHz, CDCl3) δ 2.65 (m, 2H) 3.16 (m, 2H) 3.82 (m, 1H) 4.59 (s, 2H) 5.23 (s, 2H) 7.06 (d, 1H) 7.10 (s, 1H) 7.18 (d, 1H) 7.38 (s, 1H)

1. washwas then washed with 10% MeOH/DCM (200 mL)
2. concentrationCombined organics were concentrated
3. custompartitioned between ethylacetate and saturated sodium carbonate solution
4. concentrationThe organic layer was concentrated
5. customto give a light yellow oil which
6. customwas purified on silica eluting with 5.5% 2M NH3-MeOH/DCM