Acetic Acid → HCID 66973000, compound

Participants

Reaction Steps

A mixture of tert-butyl (4,6-difluoro-1-formyl-2,3-dihydro-1H-inden-1-yl)carbamate from Step F (890 mg, 2.99 mmol), methyl 1-aminocyclopentanecarboxylate (4.25 g, 29.7 mmol, described in Intermediate 25), and AcOH (2.10 mL, 36.7 mmol) in MeOH (32 mL) was stirred at ambient temperature for 20 min. NaCNBH3 (405 mg, 6.44 mmol) was added and the pH of the mixture was checked and adjusted to pH˜5 as necessary by addition of AcOH. The reaction mixture was stirred at ambient temperature for 23 h, then quenched with saturated aqueous NaHCO3 (80 mL) and extracted with EtOAc (200 mL). The organic extract was washed with H2O (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc-100:0 to 30:70, to give the title compound. MS: m/z=425 (M+1).

Provenance & Evidence