HCID 59424371, compound → HCID 59424399, compound

HRID 1172356Notes

Reaction equation

HRID 1172356 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 (2.4 mmol, 950 mg) was dissolved in acetic acid (20 mL). Iron (17.7 mmol, 1.0 g) was added to the mixture. Reaction was heated at 85° C. and held with stirring for 1.5 hours. Mixture was cooled to room temperature then diluted with water (30 mL). Solids were decanted off. The aqueous solution was concentrated in vacuo. 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. Mixture was filtered. Filtrate layers were separated. Aqueous layer was extracted 1× ethyl acetate. Combined organic layers were dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained without further purification as yellow oil in 69% yield. MS m/e (M+H)+=335.3.

Workup

  1. customReaction
  2. temperatureMixture was cooled to room temperature
  3. customSolids were decanted off
  4. concentrationThe aqueous solution was concentrated in vacuo
  5. additionResidue was treated with ethyl acetate (50 mL)
  6. additionCelite was added to the resulting suspension
  7. filtrationMixture was filtered
  8. customFiltrate layers were separated
  9. extractionAqueous layer was extracted 1× ethyl acetate
  10. dry with materialCombined organic layers were dried (magnesium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9eda2815b40f487cb89ec91be076546e
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

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