Methyl iodide → HCID 57678971, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.22 grams (0.524 mmole) (+/−)-[6-(3-fluoro-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester in 10 mL DMF was added 0.08 grams (0.576 mmole) potassium carbonate and 0.033 mL (0.524 mmole) iodomethane. The reaction mixture was stirred at 23° C. for 0.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water saturated aqueous sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was dissolved in 3 mL warm TFA and immediately concentrated under reduced pressure. The residue was partitioned between saturated aqueous sodium carbonate ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-fluoro-N-methyl-benzenesulfonamide was isolated as the crystalline oxalate salt, 0.06 grams (18%), m.p. 176-177° C., M+H=349.

Provenance & Evidence