Diisobutylaluminumhydride → HCID 118059881, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl [{[(tert-butoxycarbonyl)(4-methoxybenzyl)amino]sulfonyl}(4-methoxybenzyl)amino]acetate (5.30 g, 10 mmol) in dichloromethane (20.0 mL) at −78° C. under N2 was treated with 1.0 M diisobutylaluminum hydride in dichloromethane (12.2 mL, 12.2 mmol, 1.22 equiv.). The reaction mixture was stirred at −78° C. for 3 h. The reaction was then quenched with methanol (3 mL) and treated with dichloromethane (100 mL) and a saturated solution of sodium potassium tartrate (150 mL). This solution was stirred at room temperature overnight. The aqueous layer was then extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was washed with brine, dried over sodium sulfate and concentrated. The residue was then purified on silica gel (0-30% ethyl acetate/hexane gradient elution) to give the desired product (3.45 g, 71%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.24 (s, 1H), 7.23 (m, 4H), 6.88 (m, 4H), 4.68 (s, 2H), 4.31 (s, 2H), 4.07 (s, 2H), 3.72 (s, 3H), 3.71 (s, 3H), 1.40 (s, 9H).

Provenance & Evidence