Aluminium lithium hydride → HCID 59030571, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]decane-8-carboxylic acid methyl ester (1.02 g, 3.67 mmol) in THF (15 mL) was added LAH (1.0 M in Et2O, 3.67 ml, 3.67 mmol) dropwisely at −45° C. for 10 min. After being stirred at −45° C. for 3 h, the reaction was quenched by adding H2O (150 μL), 15% aqueous NaOH (150 μL), and H2O (450 μL) successively and stirred at 25° C. for 1 h. The resulting inorganic gel was removed by filtration and the filter cake was rinsed with EtOAc. The combined filtrates were then concentrated under reduced pressure and purification of the residue by flash chromatography (SiO2, 90-100% EtOAc/Hexanes, gradient elution) gave (8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]dec-8-yl)-methanol (518 mg, 2.07 mmol, 56%) as a colorless liquid.

Provenance & Evidence