Potassium tert-butoxide → HCID 58817635, compound

HRID 1986936Notes

Reaction equation

HRID 1986936 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=2F)=[N:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 72434543HCID 72434543, compound

Product 1

HCID 58817635HCID 58817635, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature mixture of 4-[(2-Fluoro-3-methoxy-phenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester (5.00 g, 14.2 mmol) in THF (50 mL) under nitrogen was added potassium tert-butoxide (15.0 mL of a 1M THF solution, 15.0 mmol) rapidly and the reaction refluxed for 4 h. After cooling to room temperature, the reaction was diluted with ethyl acetate (250 mL) and washed with water (100 mL) and brine (100 mL) successively. The organics were dried over magnesium sulfate, filtered, and concentrated to give a waxy solid. Recrystallization of the solid did not remove impurities so the crude product was chromatographed on silica using a step gradient elution of 10% ethyl acetate/dichloromethane to 40% ethyl acetate/dichloromethane to afford 3.04 g (64%) of the desired product as a white powder, mp: 130-132° C.

Workup

  1. temperaturerefluxed for 4 h
  2. washwashed with water (100 mL) and brine (100 mL) successively
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a waxy solid
  7. customRecrystallization of the solid
  8. customdid not remove impurities so the crude product
  9. customwas chromatographed on silica using
  10. washa step gradient elution of 10% ethyl acetate/dichloromethane to 40% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-399b6e4ad0b642508e593d2e9aeab840
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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