4-Methylmorpholine → HCID 178501297, compound

Participants

Reaction Steps

L-Proline methyl ester hydrochloride (0.03 g, 0.18 mmol) was added to a stirred solution of the product from Example 37C (0.05 g, 0.17 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (0.042 g, 0.22 mmol), 1-hydroxybenzotriazole hydrate (0.03 g, 0.22 mmol) and N-methyl morpholine (0.1 mL, 0.87 mmol) in N,N-dimethylformamide (4 mL) at room temperature. The reaction was stirred at room temperature for 12 h and then quenched by addition of water. It was then extracted with ethyl acetate (3×25 mL), the organic extracts washed with water, brine, dried (MgSO4) and concentrated to afford the titled compound as a clear oil. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.09-1.18 (m, 2 H), 1.40-1.51 (m, 2 H), 1.75-1.86 (m, 6 H), 1.88-1.94 (m, 2 H), 2.13-2.27 (m, 3 H), 2.40-2.49 (m, 1 H), 3.51-3.58 (m, 2 H), 3.61 (s, 3 H), 4.30 (dd, J=10, 5 Hz, 1 H), 6.64 (d, J=3 Hz, 1 H), 7.27 (d, J=10 Hz, 2 H), 7.66-7.72 (m, 3 H).

Provenance & Evidence