Aluminium lithium hydride → HCID 66588630, compound

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Reaction Steps

Compound 25 (0.34 g dissolved in THF (5 mL)) was added to a suspension of LAH (0.3 g) in THF (5 mL) at 0° C. The mixture was stirred at for 40 min, before it was quenched with ice/water and basified with 27% aqueous NaOH. The product was extracted into 2-methyl-THF. The organic layer was washed with sat. aqueous NaHCO3, dried (MgSO4), and concentrated in vacuo. The residue was dissolved in MeOH (3 mL) and treated with a few mg of 5% Pd/C, 37% aqueous HCl (10 drops), and hydrogen gas (3 bar) at 50° C. for ˜1 h and further at rt (1 bar hydrogen pressure) overnight. Next morning, a few mg of additional 5% Pd/C were added, and the mixture was hydrogenated (3 bar) at 50° C. overnight (this procedure was repeated several times over a total of four days). The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was partitioned between 2M aqueous NaOH and DCM. The organic layer was washed with sat. aqueous NaHCO3, dried (MgSO4), and diluted with 2M HCl in Et2O and concentrated in vacuo. The residue was dissolved in MeOH, and treated with 2M HCl in Et2O at 0° C. The precipitated product was isolated by filtration. Yield of example 5d1: 53 mg as a white solid. LC/MS (method 111): RT 0.71 min, ELSD 100%, UV 61%. MH+: 274.1.

Provenance & Evidence