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

HRID 458446Notes

Reaction equation

HRID 458446 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=O.N1CCCCC1.[CH2:19]([O:21][C:22](=[O:38])[CH2:23][C:24]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:25])[CH3:20]>C1C=CC=CC=1>[C:34]([O:33][C:31]([N:27]1[CH2:28][CH2:29][CH2:30][C@H:26]1[C:24](=[O:25])/[C:23](/[C:22]([O:21][CH2:19][CH3:20])=[O:38])=[CH:1]/[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:32])([CH3:36])([CH3:37])[CH3:35]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 113441872-(4-formylphenyl)acetic AcidHCID 57407385(S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidine

Product 1

HCID 69516383{4-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]phenyl}acetic acidYield 34%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-formylphenylacetic acid (4.31 g, 26.3 mmol) in benzene (75 ml) and piperidine (0.95 ml, 9.5 mmol) was added tert-butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1-pyrrolidinecarboxylate (8.1 g, 28.4 mmol). The solution was refluxed under a Dean-Stark trap for 8 h. The solvent was removed by rotary evaporation. The product was purified by silica gel column chromatography (silica gel/75% ethyl acetate in petroleum ether) giving A as an off-white solid (3.81 g, 34% yield). LCMS m/z 432 (MH)+.

Workup

  1. temperatureThe solution was refluxed under a Dean-Stark trap for 8 h
  2. customThe solvent was removed by rotary evaporation
  3. customThe product was purified by silica gel column chromatography (silica gel/75% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e541197302f148fa85e22fe711622b00
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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