Sodium cyanoborohydride → tert-Butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

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Reaction Steps

To a stirred solution of tert-butyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (196 mg, 0.52 mmol) in MeOH (20 mL) were added NH4OAc (795 mg, 10.3 mmol) and NaCNBH3 (324 mg, 5.2 mmol). The mixture was heated at reflux for 1 d. The mixture was concentrated under reduced pressure, diluted with EtOAc (90 mL), washed with 1M aq NaOH (25 mL) and dried over Na2SO4. Removal of the solvent gave crude (±)-tert-butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (264 mg) which was used without purification.

Provenance & Evidence