Diisobutylaluminum hydride → HCID 86698559, compound

Participants

Reaction Steps

To a solution of 169.7 mg of methyl ester 29 in 2 mL of dichloromethane was added 1.43 mL of DIBAL-H (1M in toluene, 3 eq) dropwise at −78° C. under Ar protection. After addition, the reaction mixture was stirred at the same temperature and stirred for additional 2 h then 5 mL of aqueous saturated sodium potassium tartrate was added by syringe. The reaction mixture was allowed to warm to room temperature and stirred for additional 4 h. After separation, the aqueous layer was extracted with three portions of 5 mL of dichloromethane. The combined organic layer was washed with brine and dried over magnesium sulfate. After the solvent was removed, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:2 EtOAc-hexanes gave product 30 as white solid: yield 148 mg, (95%). Silica gel TLC Rf 0.20 (1:1 EtOAc-hexanes); 1H NMR (CDCl3, ppm): δ 1.72 (br s, 1H), 2.52 (s, 3H), 2.96 (s, 3H), 3.08 (t, J=8.4 Hz, 2H), 3.54 (t, J=8.4 Hz, 2H), 4.58 (s, 2H). 13C NMR (CDCl3, ppm): δ 22.01, 23.97, 32.29, 51.78, 76.68, 111.48, 114.08, 149.79, 159.93, 164.67; HRMS (ESI+) calculated for C11H13N2O4SF3 (M+H+) 327.0621. found 327.0622.

Provenance & Evidence