Water → HCID 57733422, compound

Participants

Reaction Steps

To a solution of 3-bromomethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (83 mg, 0.174 mmol) in THF (1.5 ml, anhydrous) and DMF (1.5 ml, anhydrous) sodium cyanide (83 mg, excess) was added. After 5 min the obtained suspension was poured into water (50 ml) followed by addition of heptane (20 ml). The crude product was separated by filtration and purified by flash chromatography on SiO2 (5 g, 1:1 EA-heptane) to give 50 mg of colourless solid, yield 68%. LC-MS (m/z) 422.4 (MH+); tR=1.39. 1H NMR (250 MHz, DMSO-d6, T=343 K): 0.94 (t, 3H), 1.78 and 1.85 (two overlapping qui of ABX4, 2H, CH2 of Et), 3.45 and 3.54 (two d of AB, 2H, CH2CN), 4.98 (q, 1H), 7.22-7.44 (m, 8H), 7.53-7.64 (m, 4H), 7.72 (dt, 1H), 8.25 (dd, 1H), 9.05 (d, 1H).

Provenance & Evidence