Formaldehyde → HCID 71112454, compound

Participants

Reaction Steps

tert-Butyl 4-((2,2-diphenylacetyloxy)methyl)piperidine-1-carboxylate (prepared as in Preparation intermediate 12 with 2,2-diphenylacetic acid replacing cyclohexylmandelic acid) (0.40 g, 0.98 mmol) in THF (5 mL) was treated with lithium hexamethyldisilazide (1.17 mL, 1.17 mmol, 1.0 M solution in THF) followed by formaldehyde (0.20 g, 50% w/w). The reaction mixture was stirred at RT for 16 hours then quenched with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 30-60% ethyl acetate in petroleum ether (40:60) to afford the title compound (0.10 g, 23%).

Provenance & Evidence