反应详情

温度

120 °C

A mixture of polyphosphoric acid (150 g) and 2-(phenylmethyl)cyclohexanone, oxime (9 g, 45 mmol), which had been prepared as described by W. G. Kofron et al., J. Org. Chem., 41, 439 (1976), was heated with manual stirring to 120° C. for 20 minutes and then at 130° C. for ten minutes. The hot solution was poured onto 1000 g of ice, the pH adjusted to 4 with solid NaOH, and extracted 3× with EtOAc. After washing with brine, drying over Na2SO4, and concentration, the residue was chromatographed on silica gel using 1:1 EtOAc/hexane to elute a 1:1 mixture of the two isomeric lactams. The mixture was separated by prep HPLC using a C18 reverse phase YMC S15 column with 68% solvent B as eluant to yield 2.3 g (26%) of the title compound and 1.8 g of the isomeric hexahydro-3-(phenylmethyl)-2H-azepin-2-one.

1. customhad been prepared
2. temperature, 41, 439 (1976), was heated with manual
3. waitat 130° C. for ten minutes
4. extractionextracted 3× with EtOAc
5. washAfter washing with brine
6. dry with materialdrying over Na2SO4, and concentration
7. customthe residue was chromatographed on silica gel using 1:1 EtOAc/hexane
8. washto elute
9. additiona 1:1 mixture of the two isomeric lactams
10. customThe mixture was separated by prep HPLC