Pyridine → HCID 57554623, compound

HRID 1511873Notes

Reaction equation

HRID 1511873 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.C(O)(C(F)(F)F)=O>CS(C)=O.C1(C)C=CC=CC=1>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 57554794HCID 57554794, compound

Product 1

HCID 57554623HCID 57554623, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-(4-octylphenyl)pyrrolidin-3-ol (3.7 g, 13.43 mmol) in DMSO (50 ml) and Toluene (50.0 ml) at 0° C. was added pyridine (3.80 ml, 47.0 mmol), DCC (4.85 g, 23.51 mmol), and TFA (1.035 ml, 13.43 mmol). Following the addition the reaction mixture was allowed to warm to room temperature. After 5 h saturated NaCHCO3 was added to the reaction mixture and the suspension was filtered. The filtrate was partially concentrated in vacuo and the resulting dark oil was extracted with heptane. The heptane extracts were purified by silica gel chromatography eluting with EtOAc/Hep to provide 1-(4-octylphenyl)pyrrolidin-3-one (3.1 g, 11.34 mmol, 84% yield) as a colorless solid.

Workup

  1. additionthe addition the reaction mixture
  2. filtrationthe suspension was filtered
  3. concentrationThe filtrate was partially concentrated in vacuo
  4. extractionthe resulting dark oil was extracted with heptane
  5. customThe heptane extracts were purified by silica gel chromatography
  6. washeluting with EtOAc/Hep

Sources & evidence

ORD record
ord-c0132831b7b04796a64b2fd4bf079d46
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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