Diisobutylaluminum hydride → HCID 57857033, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−65 to −75° C.) solution consisting of (3aR,4R,5R,6aS)-4-((3R,E)-3-(benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (intermediate 30, 0.369 mg, 0.740 mmol) in toluene (8 mL) was added a solution consisting of DIBAL-H in toluene (1 M, 1.11 mL) over the course of ten seconds. The reaction mixture was stirred for two hours and was complete as judged by TLC. The reaction mixture was warmed to 10° C. and was subsequently quenched with a 7:1 mixture of THF-water (8 mL). The reaction mixture was allowed to stir overnight (18 hours). After stirring overnight a white solid had formed. The reaction mixture was decanted away and the solid was washed with 50% brine in water (3×30 mL). The organic layer was separated, dried over sodium sulfate, filtered, and the filtrate was evaporated to afford the title intermediate 31 (413 mg, 112% crude) as a yellow-green oil; MS (+cAPCI) m/z 523 (m+Na+); 1H NMR (CDCl3), δ 7.70-8.00 (m, 2H), 7.20-7.40 (m, 3H), 5.40-5.50 (m, 3H), 4.55-4.95 (m, 5H), 1.20-2.60 (m, 20H).

Provenance & Evidence