Hydrochloric Acid → HCID 178484140, compound

Participants

Reaction Steps

4M HCl in dioxane (6.05 ml) was added to a solution of example 390, tert-butyl ({trans-3-[2-fluoro-3-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)methylcarbamate (1.9 g, 4.84 mmol) in 2 ml of dioxane. The mixture was stirred for 20 h and evaporated to dryness. The residue was recrystallized from MeOH-Et2O. The crystals were separated by filtration and dryed, then CH2Cl2 (30 mL) and saturated 10N NaOH (pH 12) were added under stirring. The layers were separated; the water solution was extracted with CH2Cl2 (3×20 mL). The combined extracts were dried (Na2SO4) and evaporated; the residue was dried in vacuo to give the title compound (1.1 g, 79%) as a yellow oil. LC/MS data: 294.4, 293.4 (M+H) (calculated for C17H25FN2O 292.5). 1H NMR-data (DMSO-d6): 6.98-7.04 (m, 1H, Ar—H); 6.88-6.94 (m, 1H, Ar); 6.78-6.84 (m, 1H, Ar—H); 4.77-4.86 (m, 1H), 3.60 (s, 2H); 2.57 (d, 2H, J=7.4 Hz); 2.33-2.47 (m, 5H); 2.30 (s, 3H, NCH3); 2.20-2.28 (m, 4H); 1.64-1.73 (m, 4H).

Provenance & Evidence