1,1-Dimethylethyl 4-(3-{6-[(2,2-dimethylpropanoyl)amino]-2-fluoro-3-pyridinyl}-3-oxopropyl)-1-piperidinecarboxylate → Tert-butyl 4-[3-(6-amino-2-methoxy-3-pyridinyl)-3-oxopropyl]-1-piperidinecarboxylate

HRID 489791Notes

Reaction equation

HRID 489791 reaction equation
CC(C)(C)C([NH:5][C:6]1[N:11]=[C:10](F)[C:9]([C:13](=[O:29])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1)=O.C[C:33](C)([O-:35])C.[K+]>CO.O>[NH2:5][C:6]1[N:11]=[C:10]([O:35][CH3:33])[C:9]([C:13](=[O:29])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 222626761,1-Dimethylethyl 4-(3-{6-[(2,2-dimethylpropanoyl)amino]-2-fluoro-3-pyridinyl}-3-oxopropyl)-1-piperidinecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22262602Tert-butyl 4-[3-(6-amino-2-methoxy-3-pyridinyl)-3-oxopropyl]-1-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-(3-{6-[(2,2-dimethylpropanoyl)amino]-2-fluoro-3-pyridinyl}-3-oxopropyl)-1-piperidinecarboxylate (step 2, 360 mg, 0.827 mmol) and potassium tert-butoxide (278 mg, 2.48 mmol) in methanol (8 ml) was refluxed for 1 h. After cooling to room temperature, the mixture was diluted with water (20 ml) and extracted with diethyl ether (100 ml×2). The combined organic layer was washed with water (50 ml) and brine (50 ml), and dried over magnesium sulfate. Removal of the solvent gave 300 mg (100%) of the title compound as a colorless gum.

Workup

  1. temperaturewas refluxed for 1 h
  2. extractionextracted with diethyl ether (100 ml×2)
  3. washThe combined organic layer was washed with water (50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-959268d708b4466d8c09f4329e1a4c5a
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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