(-)-Myrtanol → 5-chloro-4-(((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methoxy)-2-fluoro-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

Following the procedure as described in Example 1 and making variations as required to replace 2-cyclopropylethanol with ((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]-heptan-2-yl)methanol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)-benzamide, the title compound was obtained as a colorless solid (0.03 g, 2%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (s, 1H), 7.76 (d, J=7.4 Hz, 1H), 7.25 (d, J=12.5 Hz, 1H), 3.96 (d, J=6.8 Hz, 2H), 3.35 (s, 3H), 2.47-2.37 (m, 1H), 2.10-2.03 (m, 1H), 1.94-1.65 (m, 5H), 1.48-1.37 (m, 2H), 1.12 (s, 3H), 0.85 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.3 (d, J=2 Hz), 159.8 (d, JC-F=255 Hz), 158.1 (d, JC-F=11 Hz), 130.7 (d, JC-F=3 Hz), 116.6 (d, JC-F=3 Hz), 113.7 (d, JC-F=14 Hz), 102.5 (d, JC-F=28 Hz), 73.1, 41.9, 41.2, 40.1, 38.8, 34.1, 26.5, 23.5, 23.1, 20.0, 17.4; MS (ES−) m/z 402.1, 404.1 (M−1).

Provenance & Evidence