Trifluoroacetic acid → 4-Methyl-4,6,7,8,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepin-3(2H)-one

HRID 1668568Notes

Reaction equation

HRID 1668568 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][C:9]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11][C:10]=3[CH:23]=[C:6]2[O:5][CH2:4][C:3]1=[O:24].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[C:7]2=[CH:8][C:9]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:10]=3[CH:23]=[C:6]2[O:5][CH2:4][C:3]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584947921,1-Dimethylethyl 4-methyl-3-oxo-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

Product 1

HCID 584946054-Methyl-4,6,7,8,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-methyl-3-oxo-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate (0.16 g) was treated with TFA (2 ml) in DCM (4 ml) for 3 h at 25° C. After elimination of volatiles under reduced pressure the residue was partitioned between aqueous NaHCO3 and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were dried (Na2CO3), filtered and concentrated to give the title compound as a colourless solid which was used without further analysis (0.11 g).

Workup

  1. customAfter elimination of volatiles under reduced pressure the residue was partitioned between aqueous NaHCO3 and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. dry with materialThe combined DCM layers were dried (Na2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc0c507d78a34d4486163d449c6b3279
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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