Ethyl formate → HCID 19882603, compound

Participants

Reaction Steps

The product from Example 2 was converted to the free base (15q) then dissolved in toluene (40 ml). Ethyl formate (70ml) was added and the reaction refluxed for 2 hr. The solvent was evaporated giving an oil. This was dissolved in dry tetrahydrofuran (THF) (100 ml) and added dropwise to lithium aluminum hydride (3.23 g) in THF, with cooling. Upon complete addition, the reaction was refluxed for 21/2 hr. then stirred an additional 24 hr at room temperature, followed by an additional 3 hrs refluxing. The mixture was cooled in an ice bath, then quenched with H2O (3.3 ml), 15% aq. KOH (3.3ml) and H2O (9.9ml) added dropwise. After stirring for 1 hr at room temperature, the reaction was filtered, and evaporated to dryness. The residue was converted to the HCl salt with ethereal/HCl giving 12.9 g desired product.

Provenance & Evidence