Calcium Chloride → HCID 402597, compound

Participants

Reaction Steps

Activated zinc (89.0 g, 1.36 mol) and calcium chloride (44.0 g, 0.40 mol) were added to a solution of (6R)-1-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (3) (20.0 g, 56.8 mmol) in 50% EtOX (1000 ml). The reaction mixture was refluxed for 18 hours and filtered on Celite. The filtrate was concentrated by evaporation, the residue was diluted with 2N hydrochloric acid (500 ml) and extracted with EtOAc (3×400 ml). The pH of the aqueous phase was set at above 8.5 with concentrated ammonia and extracted with CH2Cl2 (3×100 ml) and with CH2Cl2:MeOH=9:1 (3×100 ml). The combined organic extracts were washed with brine (200 ml), dried (Na2SO4) and concentrated by evaporation to produce 12.3 g (79.0% of compound 4: 1H-NMR (CDCl3) δ 6.62 (b, 2H), 6.02 (m, 2H), 4.61 (b, 1H), 4.14 (t, J=4.3 Hz, 1H), 3.98 (d, J=5.0 Hz, 2H), 3.83 (s, 3H), 3.30 (m, 1H), 2.69 (t, J=15.7, 1H), 2.10–1.63 (m, 4H); 13C-NMR (CDCl3) δ 146.2 (s), 144.1 (s), 133.1 (s), 131.7 (s), 127.8 (d), 126.8 (d), 120.8 (d), 111.1 (d), 88.4 (d), 61.9 (d), 55.9 (q), 53.3 (t), 48.5 (s), 46.7 (t), 39.4 (t), 29.9 (t). Anal. (C20H26N2O4) C, H, N.

Provenance & Evidence