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

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.

1. customThe lower layer was removed via pipette
2. concentrationThe upper pentane layer was concentrated in vacuo
3. dissolutionthe resulting residue was dissolved in THF (100 mL)
4. customTo the stirred reaction
5. stirringto stir overnight at room temperature
6. customAfter quenching with Na2SO3 and NaHCO3
7. customthe reaction was partitioned between CH2Cl2 and water
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo to a dark yellow oil (9.5 g) that
10. customwas used without further purification

ORD record

ord-4e533b5a68504ea2938d3df58ddee90b

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345708B2