Methyl chloroformate → 2-Dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene

HRID 274797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274797
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.Cl[C:31]([O:33][CH3:34])=[O:32]>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([C:31]([O:33][CH3:34])=[O:32])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Komponenten

7

Edukt 4

HCID 6586Methyl chloroformateHCID 8058HexaneHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 101082452-Dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthaleneAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Alternatively, to a solution of 8-bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene (220 mg, 0.71 mMol) in tetrahydrofuran (5 mL) at -78° C. was added a solution of n-butyl lithium in hexane (1.6 M, 1 mL, 1.6 mMol), and the solution was stirred for two hours at -78° C. The solution was then cannulated into a solution of methyl chloroformate (0.5 mL, 6.5 mMol) in tetrahydrofuran (10 mL) at -78° C., and the reaction mixture was allowed to warm gradually to room temperature. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and was then extracted with diethyl ether. The combined extracts were dried over sodium sulfate and evaporated in vacuo to give a greenish-yellow oil. Purification by flash chromatography (3:1 hexane:tetrahydrofuran+tr. NH4OH) gave the title compound as a colorless glass (130 mg, 63%). The hydrochloride salt was formed and recrystallized (acetone/diethyl ether) to give colorless crystals (m.p.=132° C.).

Aufarbeitung

  1. temperatureto warm gradually to room temperature
  2. extractionwas then extracted with diethyl ether
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give a greenish-yellow oil
  6. customPurification by flash chromatography (3:1 hexane:tetrahydrofuran+tr. NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-32dd8015b42d47f3a5701d39217337df
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389687

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