HCID 86663725, compound → HCID 66833158, compound

Participants

Reaction Steps

A solution of 2-(benzhydrylidene-amino)-2-benzoyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hexanoic acid tert-butyl ester (186 mg, 0.32 mmol) in 6 N HCl (6 mL) was stirred at 65° C. for 1 day. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (5 mL) and washed with dichloromethane (3×5 mL). The aqueous layer was frozen in liquid nitrogen and lyophilized to give 2-amino-6-borono-1-phenyl-hexan-1-one (76.5 mg, 88%). 1H NMR (D2O, 300 MHz) δ 8.04-7.60 (m, 2H), 7.77 (tt, J=7.6, 1.2 Hz, 1H), 7.61 (d, J=7.6 Hz, 2H), 5.18 (dd, J=7.5, 4.7 Hz, 1H), 2.15-1.82 (m, 2H), 1.5-1.2 (m, 4H), 0.69 (t, J=7.2 Hz, 2H).

Provenance & Evidence