Triethylamine → N-Methoxy-N-methyl-3-methylidenecyclobutane-1-carboxamide

Temperature

0 °C

To a solution of 3-methylenecyclobutanecarboxylic acid (525 mg, 4.68 mmol, Frontiers Scientific Services) in DMF (5 mL, aldrich) was added a solution of N,O-dimethyl hydroxylamine hydrochloride (0.55 g, 5.62 mmol, Aldrich) and triethylamine (0.78 mL, 5.62 mmol, Aldrich) in DMF (5 mL, Aldrich). The reaction was cooled to 0° C. and propylphosphonic anhydride solution (50 wt. % in DMF; 4.47 mL, 7.02 mmol, Alfa Aesar) was added. The reaction was stirred at RT for 16 h. The reaction was quenched with saturated NaHCO3 (10 mL) and stirred at RT for 5 min. The reaction was extracted with EtOAc (2×30 mL) and the combined organic extracts were washed with saturated ammonium chloride (2×40 mL), dried over MgSO4, and concentrated. The residue was dissolved in diethyl ether (5 mL) and the solution mixture was washed with H2O (2×10 mL), dried over MgSO4, concentrated, and dried in vacuo to give 398 mg of the title compound as a light yellow liquid. MS (ESI, positive ion) m/z: 156.1 (M+H).

1. customThe reaction was quenched with saturated NaHCO3 (10 mL)
2. stirringstirred at RT for 5 min
3. extractionThe reaction was extracted with EtOAc (2×30 mL)
4. washthe combined organic extracts were washed with saturated ammonium chloride (2×40 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in diethyl ether (5 mL)
8. washthe solution mixture was washed with H2O (2×10 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customdried in vacuo

ORD record

ord-b2a15e92740d4d8180a58c4b6e924391

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2