Methanol → HCID 54352100, compound

Participants

Reaction Steps

To a stirred solution of 132.23 g (0.647 mol) of (S)-2-(N-Benzyl-N-cyanomethylamino)-1-propanol, from step 1b, in 500 mL of methylene chloride and 94 mL of anhydrous carbon tetrachloride under nitrogen and anhydrous conditions and at room temperature was added 170 g (0.648 mol) of triphenylphosphine. The mixture was stirred at room temperature, but soon the exothermic reaction raised the temperature to reflux temperature. The reaction was stirred for 22 hours, another 8.5 g (0.032 mol) of triphenylphosphine was added, and the reaction was stirred another 2.5 hours. Methanol was added to destroy the excess triphenylphosphine, and the mixture concentrated to dryness. The solid was triturated with ether and hexane, which were filtered and concentrated. The oil was redissolved in ether, hexane added, filtered, concentrated and chromatographed over a short silica gel column, eluting with 1:4 ethyl acetate:hexane to afford after removal of the solvent 112.31 g (77.9% yield) of the title product as a colorless liquid. MS M/Z: 223, 225 (M+H). NMR (CDCl3) d: 1.35 (3H, d, J=6 Hz), 3.21 (1H, sextet, J=6 Hz), 3.48 (2H, s), 3.52 (2H, s), 3.57 (1H, dd, J=6, J=12 Hz), 3.68 (1H, dd, J=5, J=12 Hz), 7.35 (5H, m).

Provenance & Evidence