反应详情

温度

105 °C

(S)-3-((S)-Cyclopropylhydroxymethyl)pyrrolidine-1-carboxylic acid t-butyl ester (35 mg, 140 μmol), copper(I) iodide (8.3 mg, 43.5 μmol), o-phenanthroline (15.7 mg, 87 μmol), and 1-iodonaphthalene (73.7 mg, 290 μmol) were combined. Toluene (463 μL, 4.4 mmol) was added, followed by the addition of cesium carbonate (94.5 mg, 290 μmol). Air was bubbled through the mixture, the vessel was scaled, and the mixture was heated at 105° C. for 72 hours. The mixture was filtered, rinsed with DCM, and concentrated. The crude material was treated with 1.25M HCl in EtOH (1.2 mL, 1.5 mmol) and stirred overnight. The mixture was concentrated, redissolved in 1:1 AcOH:H2O and purified by preparative HPLC to yield the title compound as a mono-TFA salt (3.5 mg, 99% purity). MS m/z: [M+H]+ calcd for C18H21NO, 268.16. found 268.2.

1. customAir was bubbled through the mixture
2. filtrationThe mixture was filtered
3. washrinsed with DCM
4. concentrationconcentrated
5. concentrationThe mixture was concentrated
6. dissolutionredissolved in 1:1 AcOH
7. customH2O and purified by preparative HPLC