Aluminium lithium hydride → [2-(5-Hydroxy-2-oxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

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Reaction Steps

[2-(2,5-Dioxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (14.6 g, 60 mmol) was dissolved in THF (1.5 L) and treated with 1.0 M LiAlH4 in THF (77 mL, 77 mmol) added dropwise. The initial vigorous effervescence subsided and the solution became opaque white. The mixture was stirred for 16 h and then quenched (i. 2.0 mL of water; ii. 2.0 mL of 4 M aqueous NaOH; iii. 10 mL of water). The mixture was filtered and the resulting filtrate concentrated to give 12.1 g of solid. This was dissolved in 100 mL of hot EtOAc and applied (hot) to 250 g of silica pre-washed with EtOAc. The product was isolated by elution with EtOAc→2% MeOH/EtOAc→5% MeOH/EtOAc as a white solid (7.85 g, 53%). The compound has poor solubility in a number of organic solvents.

Provenance & Evidence