Acetaldehyde → HCID 69812790, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 1′-benzyl-4-bromospiro[indoline-3,4′-piperidine]-1-carboxylate (0.700 g, 1.53 mmol) in THF (10 mL) at −78° C. was treated by the dropwise addition of 1.6M in hexanes n-BuLi (0.673 ml, 1.68 mmol). The mixture was stirred at −78° C. for 30 minutes, and acetaldehyde (0.129 mL, 2.30 mmol) was added neat and stirring was continued an additional 30 minutes at −78° C. The reaction was then stirred at room temperature for 1.5 hours. The reaction was quenched by the addition of saturated NH4Cl, and the reaction was extracted with EtOAc. The combined organics were washed with brine, dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (20 then 50-70% EtOAc/Hexane) to yield pure tert-butyl 1′-benzyl-4-(1-hydroxyethyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (0.491 g, 76%). LCMS (APCI+) m/z 423.2 [M+H]+; Rt=3.66 min

Provenance & Evidence