Water → HCID 59002877, compound

HRID 561121Notes

Reaction equation

HRID 561121 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9](F)=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6][N:7]2N[C@H](C1C=CC=CC=1)CO.[H-].[Na+].[OH2:33]>C1COCC1>[F:1][C:2]1[C:3]2[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6][N:7]3[C@H:4]([C:3]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:2]=4)[CH2:5][O:33][C:9]([C:8]=23)=[C:10]([F:13])[C:11]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 66999686HCID 66999686, compound

Product 1

HCID 59002877HCID 59002877, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (R)-5,6,7,8-tetrafluoro-1,4-dihydro-1-[(2-hydroxy-1-phenylethyl)amino]-4-oxo-3-quinolinecarboxylate (3.10 g, 7.57 mmol) in THF (60 mL) was added NaH (364 mg, 9.10 mmol, 60% in oil) and the mixture was stirred at room temperature for 10 h. The mixture was treated portionwise at 0° C. with water. A precipitate formed and was collected by filtration, washed successively with EtOAc and then dried to give ethyl(R)-8,9,10-trifluoro-2,3-dihydro-7-oxo-3-phenyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (329 mg, 11%) as a solid.

Workup

  1. customA precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed successively with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-b28c310afe6a4b59a9dbf790206b59c2
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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