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 1986918ノート

反応式

HRID 1986918 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 83717Copper iodide触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b835dce252d840beb1e1d31167f70c06
出典データセット
uspto-grants-2009_06
特許番号
US07550469B2

反応ノート

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