HCID 68738138, compound → HCID 68737323, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1′-benzyl-4-bromospiro[indoline-3,4′-piperidin]-2-one (12.0 g, 32.3 mmol) in THF (300 mL) was carefully treated with the addition of BH3-THF complex (97 mL, 97 mmol). The reaction was then heated at 80° C. for 24 hours. The reaction mixture was quenched by the addition of 1N HCl. The aqueous layer was extracted with EtOAc (3×100 mL). The aqueous layer was basified to a pH of 12 with NaOH pellets and extracted with EtOAc (3×200 mL). The organic layers were dried with MgSO4 and concentrated under reduced pressure to give 1′-benzyl-4-bromospiro[indoline-3,4′-piperidine] (7.3 g, 63%) as an oil. LCMS (APCI+) m/z 357/359 [M+H]+; Rt=3.07 min.

Provenance & Evidence