Hydrochloric Acid → HCID 11106179, compound

Participants

Reaction Conditions

Reaction Steps

Step D (1): To a sealed tube flushed with nitrogen was added L-proline (3.684 g, 32.0 mmol), potassium carbonate (6.634 g, 48.0 mmol), copper (I) iodide (609 mg, 3.2 mmol), iodobenzene (3.58 mL, 32.0 mmol) and N,N-dimethylacetamide. The mixture was heated at 90° C. for 48 hours, then cooled to room temperature. Water was added, and the pH adjusted to <3 with concentrated HCl. The aqueous phase was extracted 4 times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (0 to 100% EtOAc/hexane gradient) afforded N-phenylproline which was used directly in the next step. LC-MS (M+H)+=192. LC-MS RT (column 1)=2.230/4.00. 1H NMR (500 MHz, CDCl3): δ 10.574 (br s, 1H), 7.29-7.25 (m, 2H), 6.785 (t, J=7.5 Hz, 1H), 6.613 (d, J=8.0 Hz, 2H), 4.25 (dd, J=2.4, 8.8 Hz, 1H), 3.60 (dt, J=2.8, 8.3 Hz, 1H), 3.36 (m, 1H), 2.38-2.01 (m, 4H).

Provenance & Evidence