Hexane → HCID 68006436, compound

HRID 1026593Notes

Reaction equation

HRID 1026593 reaction equation
O1CCO[CH2:3][CH2:2]1.Br[C:8]1[CH:33]=[N:32][C:11]2[O:12][C:13]([CH3:31])([CH3:30])[C:14](=[O:29])[N:15]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[C:10]=2[CH:9]=1.CCCCCC.C([Zn]CC)C>O>[CH2:2]([C:8]1[CH:33]=[N:32][C:11]2[O:12][C:13]([CH3:30])([CH3:31])[C:14](=[O:29])[N:15]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:18][CH2:17]3)[C:10]=2[CH:9]=1)[CH3:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 312751,4-DioxaneHCID 68006368HCID 68006368, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 68006436HCID 68006436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, to a 1,4-dioxane solution (10.0 ml) of tert-butyl 4-(7-bromo-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (Example 52-1) (150 mg) was added a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-dichloromethane complex (69.5 mg), and then a hexane solution (1 M, 0.681 ml) of diethyl zinc was added dropwise, followed by stirring overnight. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-ethyl-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (84.8 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-32d4699f01fd4e7ba9c2019be9e2843a
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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