1-Piperidinecarboxaldehyde → HCID 178422066, compound

Participants

Reaction Steps

To a −78° C. solution of 9.04 g (25.6 mmol) 2-bromo-cis-6,7-dihydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene acetonide in 110 ml tetrahydrofuran was added 32.0 ml (51.1 mmol) of a 1.6M solution of n-butyllithium in hexanes. After 1 hour at −78° C., 5.79 g (51.1 mmol) of 1-formylpiperidine was added. After 20 minutes at −78° C., the resulting mixture was quenched with water. Upon warming to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography with elution with 5% ethyl acetate/hexane to yield 5.65 g (73%) of 3-bromo-cis-6,7-dihydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde acetonide(MH+=303).

Provenance & Evidence