Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → HCID 68379697, compound

Participants

Reaction Steps

A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (100 mg, 0.43 mmol), tert-butyl 4-aminobenzoate (83 mg, 0.43 mmol), NaHB(OAc)3 (273 g, 1.29 mmol) and AcOH (2 drops) in 30 mL of DCM was stirred at room temperature overnight. The mixture was washed with sat NaHCO3 (30 mL), water (2×30 mL), and brine (30 mL) dried over Na2SO4 concentrated under reduce pressure to give a crude tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamino)benzoate (130 mg) as a black oil. LC-MS: 410 [M+H]+, tR=1.92 min.

Provenance & Evidence