Acetic Acid → tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1.5 g) was dissolved in THF (7.5 ml) and cooled to −5° C. NaBH4 (0.212 g) was then added and the mixture was stirred for 1 h at room temperature (TLC monitoring). When the conversion was complete, acetic acid was added to the mixture and the methanol was then distilled off. The residue was taken up in water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 30% ethyl acetate/hexane). Yield: 1.2 g (80%)

Provenance & Evidence