Potassium Carbonate → HCID 67224229, compound

Participants

Reaction Steps

To a stirred solution of crude (±)-tert-butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (264 mg, 0.69 mmol) in THF (5 mL) was added 10% aq K2CO3 (10 mL), followed by Teoc-OSu (269 mg, 1.04 mmol). The mixture was stirred at rt for 3 d, diluted with ether (80 mL), washed with brine (25 mL) and dried over MgSO4. Removal of the solvent left an oil (240 mg) which was purified chromatography on a 12-g silica cartridge, eluted with a 0-50% EtOAc in hexanes gradient to afford (±)-tert-butyl 7-bromo-3-((2-(trimethylsilyl)ethoxy)carbonylamino)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (85 mg, 31% for 2 steps). LC-MS Method 1 tR=2.35 min, m/z=425, 427, 547, 549.

Provenance & Evidence