(1R,5S)-2beta-formyl-3beta-phenyltropane → (1R,5S)-2beta-n-Butyl-3beta-(p-tolyl)tropane

Participants

Reaction Steps

Using a procedure similar to that described in Example 8, except replacing the compound 18 used therein with compound 19, and replacing the ethyl phosphonium salt with the corresponding propyl phosphonium salt, the title compound 23 was prepared as a colorless oil: [α]25D −76° (c 1.5, CH2Cl2); 1H NMR (CDCl3) δ0.74 (t, 3H, J=7.2 Hz), 0.70-0.90 (m, 2H), 1.12-1.30 (m, 3H), 1.39-1.68 (m, 5H), 1.96-2.20 (m, 3H), 2.24 (s, 3H), 2.31 (s, 3H), 3.03 (dt, 1H, J=5.1 and 13.2 Hz), 3.12-3.20 (m, 1H), 3.20-3.28 (m, 1H), 7.03 (d, 2H, J=8.1 Hz), 7.08 (d, 2H, J=8.1 Hz); 13C NMR (CDCl3) δ14.2, 21.0, 22.7, 24.8, 26.4, 26.7, 30.1, 33.8, 36.0, 42.1, 46.2, 62.1, 64.7, 127.7, 128.7, 135.0, 140.7; MS m/z (%) 271 (M+, 6), 242 (2), 214 (4), 96(40), 83 (100).

Provenance & Evidence