1,4-Dioxane hydrochloride → (S)-2-(4-bromo-2-fluorophenyl)-2-((R)-5,5-dimethylpyrrolidin-2-yl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)ethanone dihydrochloride

Participants

Reaction Steps

4.0M HCl/Dioxane (0.121 mL, 0.483 mmol) was added to a solution of (S)-tert-butyl 5-((S)-1-(4-bromo-2-fluorophenyl)-2-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (0.104 g, 0.161 mmol) in DCM (1 mL). The solution stirred overnight, and the solvent was removed to yield (S)-2-(4-bromo-2-fluorophenyl)-2-((R)-5,5-dimethylpyrrolidin-2-yl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)ethanone dihydrochloride (0.0618 g, 0.0998 mmol, 62.0% yield). HPLC, 254 nm=1.988 minutes, 99.66% purity, LCMS (APCI+) 547.7 m/z [M+H]+; Retention time=2.45 minutes. 1H NMR (400 MHz, D2O) 8.58 (s, 1H), 7.54 (dd, J1=1.952 Hz, J2=9.761 Hz, 1H), 7.46 (dd, J1=1.562 Hz, J2=8.199 Hz, 1H), 7.35 (t, J=7.809 Hz, 1H), 5.32 (t, J=8.199 Hz, 1H), 4.79 (d, J=9.761 Hz, 1H), 4.40-4.31 (m, 1H), 4.0-3.9 (m, 2H), 3.82-3.62 (m, 3H), 2.30-2.28 (m, 1H), 2.27-2.15 (m, 1H), 2.02-1.84 (m, 4H), 1.58 (s, 3H), 1.44 (s, 3H), 1.29 (d, J=6.637 Hz, 3H).

Provenance & Evidence