Diisobutylaluminum hydride → HCID 67461800, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 2,2-dimethyl-propylamine (0.1 mL, 0.84 mmol) in anhydrous THF (0.6 mL) under nitrogen. Cool the solution at 0° C. and add DIBAL-H (0.79 mL, 0.79 mmol, 1M solution in toluene). Allow the mixture warm up to room temperature and stir for 2 h. Add this complex to a solution of 3-(tert-butoxycarbonyl)-7-chloro-6-(4-methoxycarbonylmethylthio-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (70 mg, 0.14 mmol) in THF (0.3 mL) and stir at room temperature overnight. Dilute with EtOAc and quench with 5% aqueous KHSO4. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate as an oil (51 mg, 65%).

Provenance & Evidence