Aluminium lithium hydride → HCID 44601273, compound

Participants

Reaction Steps

To a slurry of lithium aluminum hydride, 1.0 m solution in tetrahydrafuran (1.39 mL, 1.39 mmol) in 4 mL THF at 0° C. under nitrogen was added diethyl 2-((3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)malonate (0.240 g, 0.463 mmol) as a solution in 4 mL THF slowly dropwise via syringe, with 1 mL THF rinse. The slightly yellow reaction mixture was allowed to stir 1 h, then the bath was removed. After 4 h at ambient temperature, the reaction was judged complete. Water (0.05 mL) was added carefully dropwise under nitrogen, followed by 0.10 mL 5 N NaOH, followed by 0.15 mL water. After 1 h, the reaction mixture was filtered to remove a solid, rinsing with THF, and concentrated in vacuo. The material was adsorbed onto 2 g silica gel from DCM/MeOH and purify by silica gel chromatography, 12 g, 20-100% EA/hexanes to give 2-((3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)propane-1,3-diol as a light yellow solid. MS (ESI) m/z: calculated: 434.2; Observed: 435.1 (M++1).

Provenance & Evidence