Acetonitrile → HCID 53976005, compound

Participants

Reaction Steps

A solution of (3R)-3-(3-bromophenyl)-3-(7-benzyloxyindol-1-yl)propan-1-yl methanesulfonate (2.50 g, 4.86 mmol prepared as in Example 3, step (i)) and tetrabutylammonium cyanide (1.96 g, 7.30 mmol) in dry acetonitrile (40.0 ml) under nitrogen was heated under reflux for 24 h. The cooled solution was evaporated to yield an orange/brown oil which was taken up in ethyl acetate (200 ml), washed with water (3×100 ml), dried (Na2SO4) and the solvent removed in vacuo. Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 1:4) gave the title compound as a pale yellow oil (1.60 g, 74%). [α]D19 -129 (c=0.005 gml-1, CHCl3); Vmax (thin film)/cm-1 3064, 3033, 2932, 2872, 2247 (CN), 1575; δH (270 MHz) 2.10 (2H, m 2×propyl 3-H); 2.38 (2H, m, 2×propyl 2-H); 5.09 (2H, q, CH2Ph, 2J=10.9 Hz); 6.39 (1H, dd, propyl 1-H, 3J1,2 =9.7, 3J1,2 =5.8 Hz); 6.55 (1H, d, 3-H, 3J3.2 =3.3 Hz); 6.70 (1H, d, 6-H, Jo =7.6 Hz); 6.83 (1H, d, 4-H, Jo =7.6 Hz); 7.00 (2H, m, 5-H, 5'-H); 7.05 (1H, d, 2-H, 3J2,3 =3.0 Hz); 7.15 (1H, s, 2'-H); 7.21 (1H, d, 6'-H, Jo =8.0 Hz); 7.30 (1H, d, 4'-H, Jo =8.6 Hz); 7.38 (5H, m, 5ArH).

Provenance & Evidence