4-[1-(3-Bromo-5-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester → 4-(5-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid

HRID 1986918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986918
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[S:18][C:19]([CH3:23])=[CH:20][C:21]=2Br)=[N:15][OH:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)C>[Cu](I)I>[CH3:23][C:19]1[S:18][C:17]2[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([OH:5])=[O:7])[CH2:9][CH2:10]3)=[N:15][O:16][C:21]=2[CH:20]=1

Komponenten

3

Edukt 1

HCID 724345604-[1-(3-Bromo-5-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 231124364-(5-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 83717Copper iodideKatalysator

Versuchsvorschrift

Prepared essentially as 2211-198 except that 4-[1-(3-bromo-5-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester is used as the starting material. Two other differences are: 1) 0.05 equivalents of copper iodide is used, and 2) no partition between ethyl acetate and water accompanied by subsequent extraction with ethyl acetate is required. Purification of the residue via flash column chromatography uses a mixture of ethyl acetate: n-heptane (1:4) to yield a white solid. LC/MS (ESI), m/e 345 (MNa+), retention time 2.12 minutes. Condition II.

Aufarbeitung

  1. custom2) no partition between ethyl acetate and water
  2. extractionaccompanied by subsequent extraction with ethyl acetate
  3. customPurification of the residue via flash column chromatography
  4. additiona mixture of ethyl acetate: n-heptane (1:4)
  5. customto yield a white solid

Quellen und Nachweise

ORD-Eintrag
ord-b835dce252d840beb1e1d31167f70c06
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550469B2

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