Aluminium lithium hydride → tert-Butyl 3-(2-(5-fluoro-2-hydroxyphenyl)quinazolin-4-ylamino)-trans-4-(hydroxymethyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

trans-1-tert-Butyl 3-ethyl 4-(2-(5-fluoro-2-hydroxyphenyl)-3,4-dihydroquinazolin-4-ylamino)pyrrolidine-1,3-dicarboxylate (0.093 g, 0.19 mmol, synthesised using methods outlined in Synthesis 84) was dissolved in THF (1.8 mL) and cooled to 0° C. A 1 M solution of LiAlH4 in THF (0.375 mL, 0.38 mmol) was added dropwise and the mixture was stirred at this temperature for 15 min. The reaction was quenched with sodium potassium tartrate (2 drops) and diluted with water (10 mL). The mixture was extracted with dichloromethane (3×50 mL) and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 25% ethyl acetate in hexane to give the title compound as a yellow solid (0.026 g, 30%).

Provenance & Evidence