Triphenylphosphine → HCID 86622861, compound

Participants

Reaction Steps

Dissolve 7-chloro-6-(3-hydroxy-2,2-dimethyl-propylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (prepared as described in Preparation 30) (250 mg, 0.66 mmol) in DCM (30 mL). Add diethyl azodicarboxylate (150 mg, 0.86 mmol), and triphenylphosphine (226 mg, 0.86 mmol) and stir at 40° C. for 16 h. Quench with saturated aqueous sodium bicarbonate solution, extract with DCM three times. Combine the organic layers, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:8 EtOAc:hexanes) to provide 7-chloro-6-(3,3-dimethylazetidin-1-yl)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (175 mg, 74%). MS (ES) m/z:=361.2 [M+H]. Deprotection and the succinate salt formation of the free amine is achieved essentially as described in Example 34 to give the title compound (91 mg, 71%).

Provenance & Evidence