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 1986918노트

반응식

HRID 1986918 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 83717Copper iodide촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b835dce252d840beb1e1d31167f70c06
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550469B2

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