Diisobutylaluminum hydride → HCID 68613149, compound

Participants

Reaction Conditions

Reaction Steps

DIBAL-H (1.5M in toluene, 4.9 mL, 7.35 mmol, 2.7 equiv.) was added dropwise to a stirred solution of 4-[5-[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]-3-pyridyl]-trans-2-butenoic acid methyl ester (1.00 g, 2.75 mmol) in dry CH2Cl2 at −78° C. The mixture was stirred at −78° C. for 3 hours before the reaction was quenched by adding methanol followed by saturated aqueous sodium potassium tartrate solution. The reaction mixture was then allowed to warm to room temperature where it was vigorously stirred for 1 h. The organic layer was separated, and the aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. Filtration and solvent removal afforded the crude product, which was purified by CC (SiO2, 3% methanol in CH2Cl2) to give the title alcohol as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.17 (s, 2H), 7.24 (s, 1H), 6.60 (d, J=18.2 Hz, 1H), 6.38 (m, 1H) 4.49 (m, 1H), 4.33 (m, 1H), 4.10 (dd, J=6.1, 3.2 Hz, 1H), 3.62 (t, J=6.1 Hz, 2H), 3.20 (1H, OH), 2.31 (m, 2H), 1.39 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 156.4, 155.0, 155.0, 140.4, 136.3, 133.3, 125.5, 117.8, 79.5, 71.4, 68.4, 59.9, 46.9, 43.5, 28.3, 18.7; MS (ESI) 335 (M+H+).

Provenance & Evidence