Dimethyl Sulfate → HCID 67304650, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, a 1M solution of lithium hexamethyldisilazane in THF (1.1 ml) was added dropwise to a stirred solution of 3-tert-butoxycarbonylamino-5-methylisoxazole (Tet. Lett., 1996, 37, 3339-3342; 0.2 g) in THF (9 ml) that had been cooled to −5° C. After 10 minutes, a solution of dimethyl sulphate (0.1 ml) in THF (1 ml) was added dropwise and the resultant mixture was stirred at −5° C. for 2 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic phase was dried over magnesium sulphate and evaporated to give 3-(N-tert-butoxycarbonyl-N-methylamino)-5-methylisoxazole (0.19 g); 1H NMR: (CDCl3) 1.54 (s, 9H), 2.36 (s, 3H), 3.34 (s, 3H), 6.5 (br s, 1H).

Provenance & Evidence