Cornforth reagent → tert-butyl {(6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl}carbamate
Reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([O:26][C:27](=[O:55])[NH:28][C@@H:29]1[CH2:35][CH2:34][C@@H:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=2[F:43])[CH2:32][NH:31]/[C:30]/1=[N:44]\[CH2:45][CH:46](O)[C:47]1([C:50]([F:53])([F:52])[F:51])[CH2:49][CH2:48]1)([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[C:22]([O:26][C:27](=[O:55])[NH:28][C@@H:29]1[CH2:35][CH2:34][C@@H:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=2[F:43])[CH2:32][N:31]2[C:46]([C:47]3([C:50]([F:53])([F:52])[F:51])[CH2:49][CH2:48]3)=[CH:45][N:44]=[C:30]12)([CH3:25])([CH3:24])[CH3:23]Participants
4
Procedure
Pyridinium dichromate (765 mg, 2.035 mmol) was added to a solution of crude tert-butyl [(2Z,3R,6S)-6-(2,3-difluorophenyl)-2-({2-hydroxy-2-[1-(trifluoromethyl)cyclopropyl]ethyl}imino)azepan-3-yl]carbamate from Step A (200 mg, 0.407 mmol) in acetonitrile (5 mL). After 70 h at ambient temperature, the mixture was filtered and concentrated. Saturated aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=472 (M+1).