Dimethylformamide → HCID 59486383, Verbindung

HRID 32080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32080
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN([CH:28]=[O:29])C>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:28]=[O:29])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 10064926tert-butyl N-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 59486383HCID 59486383, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (Step C) (1.080 g, 3.311 mmol) was dissolved in THF (30 mL) and cooled to −78° C. n-Butyllithium (2.5 M) (3.311 mL, 8.276 mmol) was added drop-wise to the stirred solution. The reaction was stirred at −78° C. for 30 min and DMF (1.282 mL, 16.55 mmol) was added drop-wise and the mixture was slowly warmed to RT overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude material, which was purified by flash column chromatography to furnish the pure title compound. MS (APCI pos) 217 (M-t-Bu).

Aufarbeitung

  1. additionwas added drop-wise to the stirred solution
  2. temperaturethe mixture was slowly warmed to RT overnight
  3. customThe reaction was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fea7335b68e84aff8f79d6203751b877
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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