Sodium Hydroxide → HCID 86657786, compound

Participants

Reaction Steps

A solution of (±)-cis-4-acetoxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (41.9 mmol, 13.3 g) in THF (100 mL), MeOH (25 mL), and 2 N NaOH (25 mL) was stirred for 3 hours at room temperature. The THF and MeOH were removed under reduced pressure. The crude product was extracted from the water layer with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on a 110 g SiO2 cartridge using ethyl acetate/hexanes gradient to give (±)-cis-4-hydroxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (10.2 g).

Provenance & Evidence