Methyl 4-bromobutyrate → HCID 69002319, compound

Participants

Reaction Steps

To a solution of (R)-3-(4-Benzyl-phenoxy)-pyrrolidine (126 mg, 0.5 mmol) in anhydrous CH2Cl2 (0.5 mL) was added methyl-4-bromobutyrate (99 mg, 0.55 mmol) in CH2Cl2 (0.5 mL) and triethylamine (101 mg, 1.0 mmol. The resulting mixture was purged with nitrogen and stirred at rt for 16 h. CH2Cl2 was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with brine, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography (40% EtOA /Hexane) to obtain the product as yellow solid (71 mg, 40%): MS; m/z 354.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.65-1.72 (m, 2H), 2.18-2.39 (m, 4H), 2.54-2.63 (m, 5H), 2.78-2.82 (m, 1H), 3.57 (s, 3H), 3.85 (s, 2H), 5.78 (m, 1H), 6.78 (d, 2H, J=8.8 Hz), 7.11 (d, 2H, J=8.4Hz), 7.16-7.29 (m, 5H); HPLC (ELSD); 99%.

Provenance & Evidence