Benzaldehyde → 1-Benzylpiperidine

Participants

Reaction Steps

3-Bromo-4,5-dihydroisoxazole III-14 is dissolved in methylene chloride (0.06 M with respect to isxozaole) after which triethylamine (2.5 equiv) and benzaldehyde (1.25 equiv) are added followed by sodium triacetoxyborohydride (1.5 equiv). The reaction is allowed to stir for 16 h after which point is diluted with ethyl acetate and washed with dilute NaOH and then brine. The organic layer is then dried over sodium sulfate and concentrated under vacuum to provide crude material which was purified using flash silica gel chromatography (ethyl acetate/hexanes) to provide N-benzylpiperidine III-19 as a white solid. [M−H]−=308.1 m/z. Activity: A.

Provenance & Evidence