HCID 18782830, compound → HCID 18782827, compound

Participants

Reaction Steps

The same procedure that was used in example 1 was followed except that 2-isopropenyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was used in the place of (+)-3-pinanemethyl isothiocyanate in step D to give the titled compound as a tan solid. 2-Isopropenyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was prepared by reducing 2-isopropenyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile to the requisite amine following the procedure in step C of example 42 and subsequently converted to the isothiocyanate using step A of example 15: C.I. m/z 586 [M+1]; 1H NMR (CDCl3)δ 10.47 (br s, 1H), 8.43-8.49 (m, 4H), 7.82 (d, J=8.7 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 7.13 (m, 2H), 7.08 (m, 2H), 5.27 (s, 1H), 4.74 (m, 2H), 3.33 (dd, J=11.2, 13.9 Hz, 1H), 3.23 (d, J=13.5 Hz, 2H), 3.03-3.15 (m, 2H), 2.84 (dd, J=3.2, 13.9 Hz, 1H), 1.99-2.15 (m, 2H), 1.70 (m, 3H), 1.63 (s, 3H), 1.20 (m, 2H), 1.15 (s, 3H), 0.77(s, 3H), 0.66 (m, 1H).

Provenance & Evidence