Iodine → 4-Iodo-1-methyl-6-azabicyclo[3.2.1]octan-7-one

Participants

Reaction Steps

A solution of 1-methylcyclohex-3-ene-1-carboxamide, 52b, (5.0 g, 35.9 mmol) dissolved in 100 mL of pentane and CH2Cl2 was cooled to 0° C. and treated with triethylamine (11.0 mL, 79.0 mmol) and trimethylsilyl-triflate (14.3 mL, 79.0 mmol) sequentially. The resulting mixture was stirred for 1 hour at room temperature. The lower layer was removed via pipette. The upper pentane layer was concentrated in vacuo and the resulting residue was dissolved in THF (100 mL). To the stirred reaction was added iodine (20.1 g, 79.02 mmol) and the reaction was allowed to stir overnight at room temperature. After quenching with Na2SO3 and NaHCO3, the reaction was partitioned between CH2Cl2 and water. The organic layers were combined, dried over Na2SO4, concentrated in vacuo to a dark yellow oil (9.5 g) that was used without further purification.

Provenance & Evidence