HCID 18782847, compound → 2-Isopropyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane

Participants

Reaction Steps

The same procedure that was used in example 1 was followed except that 2-isopropyl-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-Isopropyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was prepared by reduction of 2-isopropyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile to the requisite amine following the procedure in step C of example 42 and subsequent conversion to the isothiocyanate using step A of example 15: C.I. m/z 588 [M+1]; 1H NMR (CDCl3)δ 10.45 (br s, 1H), 8.42-8.46 (m, 4H), 7.82 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.1 Hz, 2H), 7.13 (m, 2H), 7.07 (m, 2H), 5.22 (s, 1H), 3.32 (dd, J=11.2, 13.9 Hz, 1H), 3.24 (d, J=13.1 Hz, 2H), 3.01-3.10 (m, 2H), 2.92 (dd, J=3.1, 13.9 Hz, 1H), 1.96 (m, 1H), 1.76 (m, 1H), 1.59-1.70 (m, 3H), 1.32 (m, 1H), 1.24 (m, 1H), 1.14 (s, 3H), 1.05 (d, 10.2 Hz, 1H), 0.86 (d, J=6.6 Hz, 3H), 0.78 (d, J=6.9 Hz, 3H), 0.70 (s, 3H), 0.50 (m, 1H).

Provenance & Evidence