Tropic acid → HCID 68706980, compound

HRID 645480

Reaction equation

HRID 645480 reaction equation
[C:1]([OH:12])(=O)[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[OH:4][CH2:3][CH:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:1]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12]

Participants

7

Reactant 4

HCID 10726Tropic acidHCID 31268PyrrolidineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68706980HCID 68706980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tropic acid (0.12 mmol) and pyrrolidine (0.12 mmol) in DMF (20 mL) are added HOAt (0.18 mmol) and EDCI-HCl (0.18 mmol). The reaction mixture is stirred at room temperature for 14 h. The reaction mixture is diluted with water, then extracted with AcOEt. The organic extracts are successively washed with water, sat. aq, NaHCO3, H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give 3-hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic extracts are successively washed with water
  3. dry with materialsat. aq, NaHCO3, H2O and brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-15157d95db1648df88d50d6902912257
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Linked notes

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