Triethylamine → HCID 178501150, compound

HRID 16713Notes

Reaction equation

HRID 16713 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:14]1([C:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]2)=[O:13])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 178501163HCID 178501163, compound

Product 1

HCID 178501150HCID 178501150, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (20.0 g) obtained in Reference Example 1(2) is dissolved in chloroform (200 ml), and thereto are added pyrrolidine (9.2 g), 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (24.7 g) and triethylamine (13.6 g) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1) to give methyl trans-4-(pyrrolidin-1-ylcarbonyl)-cyclohexanecarboxylate (11.8 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-0d8eb541421f49f9b8ffc814d67ef97a
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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