HCID 22220589, compound → HCID 69654744, compound

Participants

Reaction Steps

Benzyl-[1-(4-nitro-phenyl)-azetidin-3-yl]-amine (which was obtained in Example 398) (1.95 g, 6.87 mmol) and (2S)-3-(9H-carbazol-4-yloxy)-methyl oxirane (Berridge et al., Int. J. Radial. Appl. Instrum., 1992, 563) (1.64 g, 6.87 mmol) was stirred at reflux in anhydrous methanol for 24 hours. Methanol was removed in vacuo and the desired product was isolated using silica gel flash chromatography to give 3.01 g of product as a yellow solid; 1H NMR (300 MHz, CDCl3) δ2.90 (m, 2H), 3.04(s, 1H), 3.85 (m, 3H), 3.98(m, 3H), 4.23(m, 3H), 6.01(d, 2H, J=7.26 Hz), 6.61(d, 1H, J=8.10 Hz), 7.06(d, 1H, J=8.04 Hz), 7.17(t, 1H, J=2.14 Hz), 7.34(m, 7H), 7.97(d, 2H, J=9.12 Hz), 8.14(t, 2H, J=8.79 Hz); MS (ES) m/z: 522.9 (MH+); Anal. Calcd. for C31H30N4O4: C, 71.25; H, 5.79; N, 10.72. Found: C, 70.77; H, 6.17; N, 9.61.

Provenance & Evidence