Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 15908470, compound

Participants

Reaction Steps

A solution of 0.98 g (4.3 mmol) of N-(3-aminopropyl)-N-methylphenylsulphonamide [preparation according to P. Daetwyler et al., Helv. Chim. Acta, 61, 2646 (1978)], 0.55 g (4.73 mmol) of tetrahydrothiopyran-4-one and a catalytic amount of camphorsulphonic acid in 50 ml of toluene is heated at reflux for 3 hours using a Dean-Stark separator. After cooling to room temperature, the Dean-Stark separator is removed, 0.54 g (5.16 mmol) of chlorocarbonyl isocyanate are added and the mixture is refluxed for another hour. The solvent is removed using a rotary evaporator and the resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient). This gives 717 mg (42% yield) of an amorphous solid.

Provenance & Evidence