Hydrochloric Acid → N-((1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-4-yl)methyl)acetamide dihydrochloride

Participants

Reaction Steps

To a solution of N-((1′-benzyl-1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)acetamide (19 mg, 0.038 mmol) in MeOH (0.4 mL) was added ammonium formate (24 mg, 0.38 mmol) and 10% Pd/C (4 mg, 20% weight). The mixture was allowed to stir at reflux for 4 h. After cooling, the reaction mixture was filtered through Celite. The filtrate was evaporated in vacuo. The crude residue was purified by column chromatography (4% 7 N ammonia in MeOH/DCM) to yield the free base, which was taken up in DCM and acidified with 2N HCl in Et2O. Removal of the solvents afforded N-((1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)acetamide dihydrochloride as a solid (12 mg, 77%). LCMS (APCI+) m/z 408 [M+H]+; Rt=1.74 min.

Provenance & Evidence