Lithiumtriethylborohydride → HCID 58066680, compound

Participants

Reaction Steps

To 2-tert-butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-benzoic acid methyl ester (3.83 g, 10.9 mmol) in THF (100 mL) at −10° C. was added lithium triethylborohydride (1M in THF; 24 mL, 24.0 mmol) slowly via syringe. The reaction was allowed to warm to room temperature and stirred for 45 minutes. Analytical LCMS indicated that starting material still remained, so the mixture was cooled to 0° C., and additional lithium triethylborohydride (1M in THF; 12 mL, 12.0 mmol) was added. The reaction was warmed to room temperature, but analytical LCMS indicated that starting material still remained. The mixture was cooled to 0° C. and additional lithium triethylborohydride (1M in THF; 5 mL, 5.0 mmol) was added. The reaction was stirred at room temperature for 1.5 hours, and then the mixture was worked-up and purified to give the title compound.

Provenance & Evidence