Diisobutylaluminum hydride → HCID 57775669, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3-benzyl-2-oxotetrahydrofuran-3-yl)carbamate (4.18 g, 14.3 mmol) in THF (100 mL) cooled to −78° C. was added DIBAL-H (57.4 mL, 57.4 mL, 1M hexane) dropwise over 15 min. The reaction mixture was stirred at −78° C. for 5 h, quenched with EtOAc, diluted with diethyl ether and aqueous Rochelle's salt. Vigorous stirring was allowed until gel break-up and layer formation. The organic layer was extracted, washed with aqueous Rochelle's salt, water, brine, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (120 g silica gel, 0 to 40% EtOAc in hexane) to give tert-butyl (3-benzyl-2-hydroxytetrahydrofuran-3-yl)carbamate (intermediate I) as a white foam (ca. 1:1 diastereomeric ratio). 1H NMR (400 MHz, CDCl3) δ 7.35-7.12 (m, 5H), 5.35 (s, 0.5H), 5.32 (s, 0.5H), 5.97 (s, 0.5H), 4.25 (s, 0.5H), 4.20-4.08 (m, 1H), 4.00-3.86 (m, 1H), 3.48-2.88 (m, 3H), 2.28-1.84 (m, 2H), 1.49 (s, 4.5H), 1.47 (s, 4.5H). MS M+Na=316.

Provenance & Evidence