Ammonium formate → HCID 71268444, compound

Participants

Reaction Steps

10% Pd/C (110 mg, 0.92 mmol) and ammonium formate (585 mg, 9.25 mmol) were added to (R)-tert-butyl(1′benzyl-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (1.00 g, 1.85 mmol) in MeOH (20 mL). The reaction was heated to reflux for 6 hours, at which point the reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give (R)-tert-butyl(1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (800 mg, 96%), which was used without further purification. Boc2O (462 mg, 2.12 mmol) was added to a solution of (R)-tert-butyl(1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (800 mg, 1.77 mmol) in DCM (25 mL). The reaction mixture was stirred overnight. The organic layer was washed with saturated aqueous NaHCO3 solution and brine, dried with MgSO4 and concentrated. The crude residue was purified by column chromatography (4:1 hexane:EtOAc) to give (R)-tert-butyl 4-((tert-butoxycarbonylamine)methyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (856 mg, 88%) as a foam. LCMS (APCI+) m/z 550 [M+H]+; Rt=4.36 min.

Provenance & Evidence