Acetic Acid → HCID 66598720, compound

HRID 447234Notes

Reaction equation

HRID 447234 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:26]([O:28]C)=O)[CH:15]([OH:25])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(OCC)(=O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH:15]([OH:25])[C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:22][C:26]2=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66598832HCID 66598832, compound

Product 1

HCID 66598720HCID 66598720, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In a 3 neck flask fitted with a nitrogen inlet, thermometer, and a mechanical stirrer, 4-[2-hydroxy-1-methoxycarbonyl-2-(2-nitro-phenyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (9.93 g, 24.3 mmoles) was dissolved in acetic acid (1.75 moles, 100 mL). Iron powder (8.90 g, 159 mmoles) was added to the vessel with stirring. The stirred mixture was slowly heated to 80° C. for 30 min and then cooled to room temperature. It was then diluted with ethyl acetate and filtered through a pad of celite. Solids were washed with 20% methanol/ethyl acetate, and then with methanol. The filtrate was concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate. The layers were separated. The resulting aqueous phase was extracted twice with ethyl acetate. The organic layers were combined. The mixture was washed twice with water and the aqueous phase was discarded. The material was dried (magnesium sulfate) filtered, and concentrated to dryness. Silica gel chromatography afforded the title compound as light yellow foam in 77% yield. MS m/e (M−H)−=345.1.

Workup

  1. customIn a 3 neck flask fitted with a nitrogen inlet
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a pad of celite
  4. washSolids were washed with 20% methanol/ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate
  7. customThe layers were separated
  8. extractionThe resulting aqueous phase was extracted twice with ethyl acetate
  9. washThe mixture was washed twice with water
  10. dry with materialThe material was dried (magnesium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4759c155892b43189810f0dc606bf2e8
Source dataset
uspto-grants-2013_07
Patent number
US08481546B2

Reaction notes

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