HCID 57794797, compound → HCID 57794763, compound

Participants

Reaction Steps

1,1-dimethylethyl methyl[((1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]carbamate (20.65 g, 54 mmol), accessed via the method of Preparation 12A, was combined with 10% palladium on activated carbon (2.00 g) in 250 mL ethyl alcohol and hydrogenated under 1 atm H2(g) for 3 h at ambient temperature. The catalyst was filtered off through celite and the filtrate concentrated to a yellow oil. The crude material was purified by flash chromatography on silica eluted with 5→25% EtOAc/DCM. Appropriate fractions were combined and concentrated to give the title compound (12.02 g, 41.2 mmol, 76%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6, 90° C.) δ 7.30-7.22 (m, 9H), 7.15 (m, 1H), 4.41 (t, J=5.1 Hz, 1H), 3.87 (d, J=14.5 Hz, 1H), 3.74 (m, 1H), 3.52 (m, 1H), 3.31 (d, J=14.4 Hz, 1H), 2.63 (s, 3H), 1.21 (s, 9H), 1.20-1.07 (m, 2H), 0.77 (m, 1H). ES-LCMS m/z 314.21 (M+Na).

Provenance & Evidence