Sodium Bicarbonate → ethyl 2-(2-cyclopentyl-5-methyl-1H-pyrrol-1-yl)acetate

HRID 1189536Notes

Reaction equation

HRID 1189536 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:9]1([C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH:9]1([C:14]2[N:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:17]([CH3:18])=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 149020451-Cyclopentylpentane-1,4-dione

Product 1

HCID 67239192ethyl 2-(2-cyclopentyl-5-methyl-1H-pyrrol-1-yl)acetateYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of ethyl 2-aminoacetate hydrochloride (2.93 g, 21.0 mmol), 1-cyclopentylpentane-1,4-dione (3.43 g, 20.4 mmol), and sodium bicarbonate (4.28 g, 51.0 mmol) in dichloromethane (20.4 mL) was heated at 50° C. for 72 hours, after which the reaction was diluted in water and extracted with dichloromethane (3×30 mL), dried (sodium sulfate), filtered and concentrated to a gold residue. Purification by silica gel chromatography (ISCO 120 g, 20 mL/min) using 0 to 35% ethyl acetate in hexanes afforded ethyl 2-(2-cyclopentyl-5-methyl-1H-pyrrol-1-yl)acetate (3.49 g, 14.8 mmol, 73% yield) as a clear colorless liquid. 1H NMR (400 MHz, CDCl3) δ (ppm): 5.84 (s, 2H, two shifts isochronous), 4.54 (s, 2H), 4.23 (q, 2H), 2.83 (m, 1H), 2.19 (s, 3H), 1.91-1.98 (m, 2H), 1.73-1.79 (m, 2H), 1.58-1.64 (m, 4H), 1.27 (t, 3H).

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated to a gold residue
  5. customPurification by silica gel chromatography (ISCO 120 g, 20 mL/min)

Sources & evidence

ORD record
ord-a36d278cc6714a978f815f1edd0d8c82
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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