Diisobutylaluminumhydride → HCID 86760334, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2Z,4S,5S,6S)-7-[[(2R,3S,4R,5S,6S,7Z)-5-[(aminocarbonyl)oxy]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]methylamino]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-2-heptenoic acid methyl ester (1.77 g, 2.5 mmol) and CH2Cl2 (15 mL) cooled to −78° C., was added a solution consisting of diisobutylaluminum hydride (1.0 M in hexane, 7.5 mL, 7.5 mmol). After stirring at 40° C. for 4 h, the mixture is quenched by adding saturated potassium sodium tartrate (10 mL). The mixture is then extracted with CH2Cl2 (3×20 mL). The combined organic layers are then dried (Na2SO4), concentrated in vacuo, and chromatographed using silica gel eluted with hexane/EtOAc (70/30) to give the desired compound (1.04 mg, 61.4%) as a colorless glassy solid.

Provenance & Evidence