Triethylamine → HCID 15646116, Verbindung

HRID 1655273

Reaktionsgleichung

Reaktionsgleichung von HRID 1655273
C[N:2]1[CH:7]2[CH2:8][C:9]([CH2:11][CH:3]1[CH2:4][CH2:5][CH2:6]2)=[O:10].[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16](Cl)=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16]([N:2]1[CH:7]2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:11][C:9](=[O:10])[CH2:8]2)=[O:17]

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 11096psi-PelletierineHCID 870632,2,2-Trichloroethyl chloroformate

Produkt 1

HCID 15646116HCID 15646116, VerbindungAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11430Potassium CarbonateKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of pseudopelletierine (52 g, 0.34 mol) in toluene (220 mL) at 50° C. was added anhydrous potassium carbonate (1.0 g), followed by the slow addition of trichloroethylchloroformate (79 g, 0.37 mol). After addition was completed (30 minutes), triethylamine (10 mL) was added. The reaction was allowed to cool to room temperature and stirred for 18 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and 1N hydrochloric acid (200 mL). After the organic layer was washed with 1N hydrochloric acid (100 mL), it was washed with aqueous 10% sodium hydroxide (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford a beige solid which was triturated with hexane (300 mL) to afford 81.4 g of crystalline solid (76% yield); mp 95°-96° C. after recrystallization from ethyl acetate-hexane. Anal. (C11H14C13NO3).

Aufarbeitung

  1. additionAfter addition
  2. additionwas added
  3. washAfter the organic layer was washed with 1N hydrochloric acid (100 mL), it
  4. washwas washed with aqueous 10% sodium hydroxide (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a beige solid which
  9. customwas triturated with hexane (300 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5ebd17a7ebf543f2aa6fdad6211aef7d
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250537

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