4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester → HCID 67410158, compound

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Reaction Steps

A 500 mL Parr bottle was charged with crude 48 (1.5 g, 2.4 mmol) and 10% Pd-on-carbon (300 mg) in reagent grade MeOH (20 mL). The mixture was pressurized to 50 PSI H2 (344.7 KPa) then shaken for 2 h. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the solids were washed with MeOH and EtOAc. The filtrate was concentrated in vacuo to afford 1.1 g of 49 which was used without further purification. 1H NMR (300 MHz, CDCl3): δ9.03 (s, 1H), 8.16 (dd, J=5.4 Hz, 8.4 Hz, 1H), 7.57 (s, 1H), 7.00 (d, J=8.7 Hz, 1H), 6.93 (t, J=8.7 Hz, 1H), 5.30 (d, J=8.7 Hz, 1H), 4.76 (m, 1H), 4.30-4.20 (m, 4H), 3.89 (m, 2H), 3.55 (m, 1H), 3.48 (s, 3H), 2.73-2.69 (m, 1H), 2.05-1.99 (m, 1H), 1.74-1.65 (m, 8H), 1.43 (s, 9H), 1.26-1.06 (m, 2H) ppm. Mass spectrum, m/z [485.3] (M+H)+.

Provenance & Evidence