(3S)-pyrrolidin-3-ol → (S,Z)-4-(2-phenyl-1-(6-(pyrrolidin-3-yloxy)pyridin-3-yl)but-1-enyl)phenol

Participants

Reaction Steps

Following the same procedure as described in example 3, (S)-pyrrolidin-3-ol (558 mg, 10 eq) was reacted with (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (100 mg, 1 eq, prepared from example 1) to give the desired product (87 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), δ 7.54 (s, 1H), 7.20-7.23 (m, 2H), 7.10-7.16 (m, 4H), 7.00(d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 6.49 (d, J=8.4 Hz, 1H), 5.28 (bs, 1H), 3.15-3.32 (m, 2H), 2.94-3.05 (m, 2H), 2.43 (q, J=7.6 Hz, 1H) 1.90-2.10 (m, 1H), 1.79-1.89 (m, 1H), 0.86 (t, J=7.6 Hz, 3H); m/z=387 [M+1]+.

Provenance & Evidence