Tetrabutylammonium Fluoride → HCID 86724983, compound

HRID 1847058Notes

Reaction equation

HRID 1847058 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:14][N:13]([C:15]2[CH:16]=[CH:17][C:18]3[O:19][CH2:20][C:21](=[O:25])[NH:22][C:23]=3[N:24]=2)[C:12](=[O:26])[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][C@H:10]1[CH2:14][N:13]([C:15]2[CH:16]=[CH:17][C:18]3[O:19][CH2:20][C:21](=[O:25])[NH:22][C:23]=3[N:24]=2)[C:12](=[O:26])[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86724984HCID 86724984, compound

Product 1

HCID 86724983HCID 86724983, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (20 ml) was dissolved 6-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.93 g, 5.12 mmol). Tetrabutyl ammonium fluoride (1M tetrahydrofuran solution; 6.14 ml, 6.14 mmol) was added to this solution and the mixture was stirred at room temperature for 7 hours. The reaction solution was concentrated under reduced pressure and ethyl acetate and water were added to the obtained residue. The aqueous layer was extracted with ethyl acetate and washed with saturated sodium chloride solution. The solution was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 667 mg (49%) of the title compound in the form of a light yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and ethyl acetate and water
  2. additionwere added to the obtained residue
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. customthe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bae8f5d6a0fc48569e4b3f04f6a0fca6
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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