Triethylamine → HCID 178501150, compound

HRID 1820924Notes

Reaction equation

HRID 1820924 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.Cl.C(N=C=NCCCN(C)C)C.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

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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-dimethylaminopropyl)-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 successively with 10% hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform, then 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 successively with 10% hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-c706aec9b42a422ab65a6bcac4428ff2
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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