Lithium borohydride → Tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate (1.7 g, 3.76 mmol) was made 0.1 M in anhydrous THF and cooled to 0° C. To this stirring suspension was added LiBH4 (0.55 g, 25.20 mmol), 2M in anhydrous THF. The resulting solution was slowly warmed to ambient temperature stirred for 14 hours. The reaction was then cooled to 0° C. and carefully quenched with saturated aqueous NH4Cl. The mixture was diluted with water and extracted with ethyl acetate two times. The combined organic layers were washed with brine then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was diluted with DCM and purified by MPLC to give tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate.

Provenance & Evidence