Potassium sodium tartarate → HCID 72388329, compound

Participants

Reaction Steps

To a solution of Compound 30 (310 mg, 0.635 mmol, 30a:30b=ca. 1:2) in dry toluene (3 mL) cooled to −78° C. was slowly added diisobutylaluminum hydride (763 μL, 0.763 mmol, 1.0 M solution in toluene), and the mixture was stirred for 1.5 h. Excess reagent was decomposed by adding an aqueous solution of saturated potassium sodium tartrate, thereby quenching reaction, and into the mixture was poured ice water, and then extracted with AcOEt. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography (13 g; 5% AcOEt/hexane) to afford Compound 31 (288.5 mg, 93%) as a mixture of two stereoisomers. The ratio of the stereoisomers constituting the mixture was ca. 1:2. It was impossible to know whether the major product was aS*,2R,6R isomer or aR*,2R,6R isomer.

Provenance & Evidence