Acetone → CBL-0137 free base

Participants

Reaction Steps

Acetone (5 mL, 68.10 mmol) was added to a solution of compound 53 (1.25 g, 4.25 mmol) in CH2Cl2 (50 mL). Then STAB (3.0 g, 14.15 mmol) was added. The mixture obtained was stirred at room temperature for 4.5 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1) and then poured into an aqueous solution of NaHCO3. The organic layer was separated. The aqueous layer was extracted with CH2Cl2. The product was dried over Na2SO4 and evaporated. The residue was purified on a column, eluent: CHCl3-MeOH 99:1→90:10. Example 7 (1.04 g, 73%) was isolated as a rapidly crystallizing oil. For the preparation of its hydrochloride, the base was dissolved in CH2Cl2. Then, a solution of HCl in dioxane was added. The mixture was evaporated to dryness. The product was washed with ether.

Provenance & Evidence