HCID 59424371, compound → HCID 59424399, compound

HRID 501977Notes

Reaction equation

HRID 501977 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([CH:19]([OH:29])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-])=O)[C:15]([O:17]C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]2[CH:19]([OH:29])[C:20]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:26][C:15]2=[O:17])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 59424371HCID 59424371, compound

Product 1

HCID 59424399HCID 59424399, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 2-(1-benzylpiperidin-4-yl)-3-hydroxy-3-(2-nitrophenyl)propanoate (950 mg, 2.4 mmol) was dissolved in acetic acid (20 mL). Iron(0) (1.0 g, 17.7 mmol) was added to the mixture. The reaction was heated at 85° C. and held with stirring for 1.5 h. The mixture was cooled to room temperature and diluted with water (30 mL). The liquid was decanted away from the solids. The aqueous solution was concentrated in vacuo. The residue was treated with ethyl acetate (50 mL). The mixture was made basic with aqueous sodium hydroxide. Celite was added to the resulting suspension to create a slurry which was in turn was filtered. The filtrate layers were separated. The aqueous layer was extracted with ethyl acetate. Combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The title compound was obtained without further purification as yellow oil in 69% yield. Mass spec.: 335.3 (MH)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe liquid was decanted away from the solids
  3. concentrationThe aqueous solution was concentrated in vacuo
  4. additionThe residue was treated with ethyl acetate (50 mL)
  5. additionCelite was added to the resulting suspension
  6. filtrationwas filtered
  7. customThe filtrate layers were separated
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. dry with materialCombined organic layers were dried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9c515d6c8be45d58ee79322efaa1841
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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