Hydrochloric Acid → HCID 54671219, compound

Participants

Reaction Steps

To a solution of 1′-(4-isopropoxy-3-methylbenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbonitrile (255 mg, 0.572 mmol) in MeOH (15.3 mL) at 0° C. was added dichlorocobalt (149 mg, 1.14 mmol) followed by portion wise addition of NaBH4 (216. mg, 5.72 mmol). The reaction mixture was allowed to stir for 15 minutes at room temperature before it was cooled to 0° C. and acidified with 1M HCl. The solvent was removed under reduced pressure, and the residue was partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (15 mL). The aqueous phase was extracted with EtOAc (2×50 mL). The combined organic phases were dried with Na2SO4, filtered and concentrated to give (1-(aminomethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-isopropoxy-3-methylphenyl)methanone (170 mg, 67%). ESI-MS m/z calc. 445.6, found 446.5 (M+1)+; Retention time: 1.45 minutes (3 min run).

Provenance & Evidence