Hydrochloric Acid → (S)-2-(4-chlorophenyl)-1-(4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((R)-morpholin-3-yl)ethanone dihydrochloride

Participants

Reaction Steps

(R)-tert-Butyl 3-((S)-1-(4-chlorophenyl)-2-(4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-oxoethyl)morpholine-4-carboxylate (0.0389 g, 0.0680 mmol) was dissolved in dioxane (1 mL) and treated with 4M hydrogen chloride in dioxane (0.425 mL, 1.70 mmol). The solution was stirred at ambient temperature overnight. The reaction was concentrated in vacuo, resuspended in dioxane and concentrated in vacuo. The residue was concentrated from MeOH (3 times) and then dissolved in MeOH. The solution was then added dropwise to Et2O to afford (S)-2-(4-chlorophenyl)-1-(4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((R)-morpholin-3-yl)ethanone dihydrochloride (20 mg, 54%). m/z 472.1/474.0; 1H NMR (400 MHz, CD3OD) d ppm 8.57 (s, 1H), 7.48 (d, 2H), 7.40 (d, 2H), 5.13-5.07 (m, 1H), 4.50 (d, 1H), 4.15-4.05 (m, 1H), 4.01-3.55 (m, 13H), 3.53-3.39 (m, 1H), 2.83-2.73 (m, 1H), 1.65-1.56 (m, 1H), 1.23 (d, 3H)

Provenance & Evidence