Potassium Carbonate → HCID 18654454, compound

HRID 1742698Notes

Reaction equation

HRID 1742698 reaction equation
[C:1]([C:4]([C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[OH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:4]([C@@H:17]1[CH2:21][CH2:20][N:19]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([OH:22])=[CH:24][CH:25]=2)[CH2:18]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842214-(2-Bromoethyl)phenolHCID 13633758(S)-2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 18654454HCID 18654454, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.1 g--see Preparation 10B), 4-hydroxyphenethyl bromide (0.072 g), anhydrous potassium carbonate (0.15 g) and acetonitrile (2 ml) was heated under reflux for 45 minutes. On cooling, the mixture was partitioned between dichloromethane (5 ml) and 10% aqueous potassium carbonate (10 ml). The layers were separated, and the aqueous layer was further extracted with dichloromethane (2×5 m]). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a foam which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield 0.035 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureOn cooling
  4. customthe mixture was partitioned between dichloromethane (5 ml) and 10% aqueous potassium carbonate (10 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with dichloromethane (2×5 m])
  7. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a foam which
  10. customwas purified by column chromatography on silica eluting with dichloromethane
  11. additioncontaining methanol (5%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37a52fd9f6924bfaa8cac4fa9fa897a1
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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