Potassium Hydroxide → HCID 23112502, compound

HRID 1986904Notes

Reaction equation

HRID 1986904 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[S:18][CH:19]=[CH:20][C:21]=2Br)=[N:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>COCCO.O.[Cu]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:17]3[S:18][CH:19]=[CH:20][C:21]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 58817650HCID 58817650, compound

Product 1

HCID 23112502HCID 23112502, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolvent2×HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
65 °C

Procedure

Add to a stirring solution of 4-[(3-bromo-thiophen-2-yl)-hydroxyimino-methyl]piperidine-1-carboxylic acid tert-butyl ester (Example 3b) (25 g., 64.2 mmol) in 2-methoxyethanol (200 mL), a solution of potassium hydroxide (7.2 g,128.4 mmol) in water (20 mL). Heat the reaction to 60° C. and then add copper powder (1.25 g). Stir at 60-70° C. for 6 h and then at ambient temperature overnight. Pour the reaction mixture into water (500 mL) and extract with EtOAc (3×). Concentrate to a dark residue and purify by column chromatography over silica gel (heptane/EtOAc, 4:1) to provide 9.8 g (50%) of a white solid.

Workup

  1. temperatureHeat
  2. customthe reaction to 60° C.
  3. customat ambient temperature
  4. customovernight
  5. extractionextract with EtOAc (3×)
  6. concentrationConcentrate to a dark residue
  7. custompurify by column chromatography over silica gel (heptane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-da331eabb3874ce9983aaa48ac689402
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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