Ammonium formate → ((2S,3R,4S)-4-Amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol

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Reaction Steps

A mixture of ((2S,3R,4S)-4-amino-4-(3-chloro-2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol (4.49 g, 8.4 mmol), ammonium formate (3.2 g, 50 mmol) and 10% palladium on carbon (500 mg) in dry MeOH (40 mL) was stirred at RT under nitrogen overnight. The catalyst was removed by filtration through Celite®—washing with methanol. The filtrate was evaporated and the residue was partitioned between DCM (100 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was further extracted with DCM (100 mL×4). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title compound (4.18 g). 1H NMR (400 MHz, MeOH-d4) δ ppm: 2.73-2.84 (m, 1 H) 3.17 (dd, J=10.03, 5.14 Hz, 1 H) 3.27 (dd, J=9.96, 3.61 Hz, 1 H) 3.65-3.79 (m, 2 H) 3.88 (dd, J=8.93, 3.06 Hz, 1 H) 4.16-4.24 (m, 1 H) 4.27 (d, J=9.05 Hz, 1 H) 6.88-7.00 (m, 2 H) 7.18-7.31 (m, 9 H) 7.38-7.45 (m, 6 H) 7.58-7.67 (m, 1 H).

Provenance & Evidence