Aluminium lithium hydride → Ammonia

Participants

Reaction Steps

To a stirred suspension of 2M Lithium aluminum hydride in THF (0.09 mL, 0.180 mmol) was added a solution of the intermediate product from Example 78, Step 1; tert-butyl [(1R,2R)-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxypropyl]carbamate (50 mg, 0.15 mmol) in THF (2 mL) dropwise at 0° C. The reaction mixture was then refluxed for 18 hours. The reaction was cooled, quenched by the addition of Na2SO4.10H2O portionwise followed by anhydrous Na2SO4 and THF (5 mL) and stirred at room temperature for 30 minutes. The suspension was filtered through arbocel and the filtrated concentrated in vacuo. The residue was purified using silica gel column chromatography twice eluting both times with 90:10:1 DCM:MeOH:NH3 to afford the title compound.

Provenance & Evidence