Sodium Hydroxide → HCID 15406763, compound
Reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@](OC)(C)C2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H]([N:55](C)C)[C@H]2O)[C@@](OC)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@@]1(O)C.[OH-].[Na+]>>[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:55][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 120 °C
Procedure
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.
Workup
- customhad been prepared
- temperature, 41, 439 (1976), was heated with manual
- waitat 130° C. for ten minutes
- extractionextracted 3× with EtOAc
- washAfter washing with brine
- dry with materialdrying over Na2SO4, and concentration
- customthe residue was chromatographed on silica gel using 1:1 EtOAc/hexane
- washto elute
- additiona 1:1 mixture of the two isomeric lactams
- customThe mixture was separated by prep HPLC
Sources & evidence
- ORD record
- ord-ac0ba44606474943b50e5bef8c20d56e
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776983
Reaction notes
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