Piperidine → 4-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]benzoic acid

HRID 458440Notes

Reaction equation

HRID 458440 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])[CH3:2].N1CCCCC1.[C:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)([OH:29])=[O:28]>C1C=CC=CC=1>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:6](=[O:7])/[C:5](/[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[CH:34]/[C:33]1[CH:36]=[CH:37][C:30]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 57407385(S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidine

Product 1

HCID 695170454-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of tert-butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1-pyrrolidinecarboxylate (5.0 g, 17.5 mmol) in benzene (50 ml) and piperidine (0.3 ml, 3 mmol) was added 4-carboxybenzaldehyde (2.63 g, 17.5 mmol), and the mixture was refluxed for 3 h. The cooled solution was washed with 0.1 N HCl twice. The aqueous layer was extracted three times with ether. The combined organic phases were dried (Na2SO4) and concentrated to give C as a tan solid (5.54 g, 76% yield). LCMS m/z 416 (M−H), 833 (2M−H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. washThe cooled solution was washed with 0.1 N HCl twice
  3. extractionThe aqueous layer was extracted three times with ether
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4bd65df298b643d681ea08624d373df6
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

Loading…