2,2-Dipropyloxirane → 3-(Tert-butyldimethylsilyloxy)-3-(3-((1-hydroxycyclohexyl)methylamino)phenyl)propanenitrile

Participants

Reaction Steps

Epoxide ring opening of 2,2-dipropyloxirane with 3-(3-aminophenyl)-3-(tert-butyldimethylsilyloxy)propanenitrile following the method used in Example 67 gave 3-(tert-butyldimethylsilyloxy)-3-(3-((1-hydroxycyclohexyl)methylamino)phenyl)propanenitrile as a colorless oil. Yield (1.5 g, 56%); 1H NMR (400 MHz, DMSO-d6) δ 7.01 (t, J=7.6 Hz, 1H), 6.63 (s, 1H), 6.57 (d, J=7.6 Hz, 1H), 6.52 (d, J=7.6 Hz, 1H), 5.22 (t, J=5.2 Hz, 1H), 4.91 (t, J=6.4 Hz, 1H), 4.21 (s, 1H), 2.84 (d, J=5.6 Hz, 2H), 2.78-2.75 (m, 2H), 1.77-1.39 (m, 10H), 0.87 (s, 9H), 0.05 (s, 3H), −0.05 (s, 3H).

Provenance & Evidence