HCID 67458832, compound → HCID 67458870, compound

HRID 554091Notes

Reaction equation

HRID 554091 reaction equation
[CH2:1]([N:3]1[CH:7]([CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]1=[O:36])[CH3:2]>C(#N)C.C(O)=O>[CH2:1]([N:3]1[CH:7]([CH2:8][OH:9])[CH2:6][CH:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]1=[O:36])[CH3:2]

Participants

4

Reactant 1

HCID 67458832HCID 67458832, compound

Product 1

HCID 67458870HCID 67458870, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

1-Ethyl-3-(phenylmethyl)-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone (0.561 g, 1.1 mmol) was stirred for 24 hrs at room temperature in a mixture of acetonitrile (21 ml) and formic acid (3 ml). The reaction was not complete at this stage so the solvent was evaporated and replaced with formic acid (10 ml) and stirring was continued for 3 hrs. Reaction was still not complete so the mixture was concentrated in vacuo (azeotroping with methanol to remove all of the formic acid) and then dissolved in methanol (20 ml). Amberlyst 15® was then added to the mixture and stirring was continued at room temperature overnight. The resin was filtered off, washing with more methanol, and the filtrate was concentrated to a gum (0.625 g). The gum was purified by automated flash silica-gel column chromatography (Biotage SP4), eluting with a 0-100% gradient of ethyl acetate in hexane, to give 1-ethyl-5-(hydroxymethyl)-3-(phenylmethyl)-2-pyrrolidinone (0.170 g) which was used in the next step.

Workup

  1. customwas evaporated
  2. customReaction
  3. concentrationwas concentrated in vacuo (
  4. customazeotroping with methanol
  5. customto remove all of the formic acid) and
  6. dissolutionthen dissolved in methanol (20 ml)
  7. additionAmberlyst 15® was then added to the mixture
  8. stirringstirring
  9. waitwas continued at room temperature overnight
  10. filtrationThe resin was filtered off
  11. washwashing with more methanol
  12. concentrationthe filtrate was concentrated to a gum (0.625 g)
  13. customThe gum was purified by automated flash silica-gel column chromatography (Biotage SP4)
  14. washeluting with a 0-100% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-ce7775e444fb49189b1ae2c7aee73e40
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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