Triethylamine → HCID 67173154, compound

Participants

Reaction Steps

(R)-1-(4-bromobenzylamino)propan-2-ol (5F2) (0.034 mol, 8.2 g) was dissolved in THF (150 ml) and triethylamine (0.051 mol, 5.12 g) was added, followed by carbonyldiimidazole (0.037 mol, 6.0 g). The mixture was stirred at room temperature for 2 hours then heated to reflux for 20 hours. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined organics were washed with water and brine before drying over sodium sulphate. The crude mixture was purified on silica eluting with 35% EtOAc/Petroleum Ether to give (R)-3-(4-bromobenzyl)-5-methyloxazolidin-2-one (5F3) 6.7 g (74%); 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 2H) 7.16 (d, 2H) 4.62 (m, 1H) 4.41-4.32 (m, 2H) 3.49 (m, 1H) 2.95 (m, 1H) 1.39 (d, 3H).

Provenance & Evidence