4-(6-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester → 4-(5-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid

HRID 2111715Notes

Reaction equation

HRID 2111715 reaction equation
C(OC(N1CCC(C2C3SC=C(C)C=3ON=2)CC1)=O)(C)(C)C.C([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([C:39]2[S:40][C:41]([CH3:45])=[CH:42][C:43]=2Br)=[N:37][OH:38])[CH2:32][CH2:31]1)=[O:29])(C)(C)C>[Cu](I)I>[CH3:45][C:41]1[S:40][C:39]2[C:36]([CH:33]3[CH2:34][CH2:35][N:30]([C:28]([OH:27])=[O:29])[CH2:31][CH2:32]3)=[N:37][O:38][C:43]=2[CH:42]=1

Participants

4

Reactant 2

HCID 588177444-(6-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl esterHCID 724345604-[1-(3-Bromo-5-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

Prepared essentially as in 29c 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.

Workup

  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

Sources & evidence

ORD record
ord-39cdd679682d42869f7268984db770b5
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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