Methyl chloroformate → HCID 21251110, compound

Participants

Reaction Conditions

Reaction Steps

The product of Example 27 (1 g, 3.93 mmol) was dissolved in Et2O (35 mL) and TMEDA (1.7 mL, 1.18 mmol) and cooled to -78° C. n-Butyllithium (4.75 mL, 11.87 mmol) was added dropwise and the reaction was allowed to stir for 15 minutes at -78° C. before warming to -10° C. for 2.5 hours. The solution was cooled back to -78° C. and methyl chloroformate (0.6 mL, 7.8 mmol) dissolved in Et2O (4.5 mL) was added dropwise. The reaction was held at -78° C. for 10 minutes and then warmed to -10° C. and allowed to stir for 1.5 hours before quenching with NH4Cl (sat). The reaction mixture was extracted 3× with EtOAc. The organics were combined, washed with brine, dried over MgSO4, concentrated in vacuo. The residue was purified by column chromatography using hexane/ethyl acetate as eluant (gradient 9/1 to 4/1) to provide 0.423 g (34%) of tert-butyl N-(4-carbomethoxy-2,6-dimethoxy-3-pyridyl)carbamate as a white solid. Electrospray Mass Spec: 312.8 (M+H)+.

Provenance & Evidence