Benzylamine → Methyl 5-((benzylcarbamoyloxy)methyl)-3-phenylthiophene-2-carboxylate

Participants

Reaction Steps

To a solution of 169 (0.900 g, 3.62 mmol) in THF was added 1,1′-carbonyldiimidazole (0.588 g, 3.62 mmol) and stirred at room temperature for 90 min. Then BnNH2 (0.396 mL, 3.62 mmol), TEA (0.505 mL, 3.62 mmol) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.546 mL, 3.62 mmol) were added and stirred at room temperature for an additional 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by ISCO (40 g column, 0-45% ethyl acetate in hexanes) to yield in 82% (1.13 g) compound 170 as a pink solid.

Provenance & Evidence