Cyclopentylamine → Methyl 2-(cyclopentylamino)acetate

HRID 875970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875970
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH:7]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>C1COCC1>[CH:7]1([NH:12][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

5

Edukt 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 60984Methyl bromoacetate

Produkt 1

HCID 22080509Methyl 2-(cyclopentylamino)acetateAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of methyl bromoacetate (17.4 mL, 188 mmol) in THF (40 mL) was dropwise added to a solution of cyclopentylamine (18.6 mL, 188 mmol) and triethylamine (26.1 mL, 188 mmol) in THF (150 mL) at 0° C. Following addition, the reaction was allowed to reach room temperature and was stirred overnight. The triethylammonium salts were filtered and rinsed with scant THF. The combined filtrates were concentrated in vacuo. The desired product was distilled from the residuals under reduced pressure to yield 20.2 g of compound 225 (68% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.73 (s, 3 H) 3.41 (s, 2 H) 3.00-3.13 (m, J=12.90, 6.39, 6.39 Hz, 1 H) 1.77-1.87 (m, 2 H) 1.67-1.74 (m, 2 H) 1.48-1.59 (m, 2 H) 1.29-1.41 (m, 2 H) ppm.

Aufarbeitung

  1. additionaddition
  2. customto reach room temperature
  3. filtrationThe triethylammonium salts were filtered
  4. washrinsed with scant THF
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. distillationThe desired product was distilled from the residuals under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2c661aaac314ec983aeea249a9399cd
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980903B2

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