Diethyl Ether → (1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamine

HRID 1455734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455734
C(O[C:4](=O)[NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)C.CCOCC>C1COCC1>[CH3:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 4569760Ethyl 1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Produkt 1

HCID 7128547(1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

(1,2,3,4-Tetrahydro-naphthalen-1-yl)carbamic acid ethyl ester (5.0 g, 22.8 mmol) is added slowly under nitrogen to a suspension of LiAlH (2.6 g, 68 mmol) in THF (50 mL). The resulting mixture is heated at 75° C. with stirring for 2 h. On cooling, Na2SO4.10H2O (15.0 g) and ether (100 mL) are added to the mixture. The resulting mixture is stirred at room temperature for 1 hour, filtered through celite, and concentrated in vacuo. 1 N HCl (20 mL) and ether (20 ML) are added to the residue. The organic layer is separated and discarded. The aqueous layer is basified with 1 N NaOH and extracted with CH2Cl2 (2×25 mL). The combined extract is washed with water (2×), dried (Na2SO4) and concentrated to give (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine as an oil. [α]RT=−10.6 (0.02, EtOH). 1H NMR (CDCl3) 7.30 (m, 1H), 7.06-7.20 (m, 3H), 3.66 (t, 1H), 2.78 (m, 2H), 2.50 (s, 3H), 1.70-2.00 (m, 4H).

Aufarbeitung

  1. temperatureOn cooling
  2. stirringThe resulting mixture is stirred at room temperature for 1 hour
  3. filtrationfiltered through celite
  4. concentrationconcentrated in vacuo
  5. addition1 N HCl (20 mL) and ether (20 ML) are added to the residue
  6. customThe organic layer is separated
  7. extractionextracted with CH2Cl2 (2×25 mL)
  8. extractionThe combined extract
  9. washis washed with water (2×)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8d8dd83b6d7748da805015e7feda6b2f
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482350B2

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