Aluminium lithium hydride → HCID 67773354, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 1-(3-hydroxyazetidin-1-yl)-2,3-dimethyl-1-oxobutan-2-ylcarbamate (Compound X) (1.07 g, 3.74 mmol) in THF (50 mL) was a 1M solution of LAH in THF (16 ml, 16.00 mmol) dropwise added (over approximately 2 min) at −20° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 30 min and heated at 60° C. over night. Additional LAH in THF (1M solution, 2 mL, 2 mmol) was added and the mixture was heated at 70° C. over night. The solvent was removed. 1,4-Dioxane (60 mL) and a 0.5M solution of LAH in ethylene glycol dimethyl ether (10 mL) was added to the residue. The resultant mixture was heated at 100° C. over night. The mixture was diluted with diethyl ether (150 mL) and the reaction was quenched with Na2SO4×10H2O. The mixture was filtered and the filtrate was concentrated under reduced pressure to give the title compound (0.8 g, quant.yield). The obtained crude product was used without further purification. LCMS (M+H)+: 187.

Provenance & Evidence