Toluene → HCID 66706709, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-tert-butoxycarbonyl-7-chloro-6-methoxycarbonylmethylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine (750 mg, 1.94 mmol) in THF (25 mL) at −78° C. under nitrogen, add 1M DIBAL in toluene (5.0 mL, 5.0 mmol) dropwise with stirring. Warm to −30° C. over 1 h and quench carefully with water. Extract with EtOAc, dry over anhydrous MgSO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to give 3-tert-butoxycarbonyl-7-chloro-6-(2-hydroxy-ethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (651 mg, 94%).

Provenance & Evidence