Sodium Hydroxide → 6-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

HRID 271683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271683
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 673647966-Bromo-2-pyrrolidin-1-ylmethyl-quinoline

Produkt 1

HCID 673633166-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Under an argon atmosphere 0.69 mL (6.87 mmol) borane-pyridine complex are added to a solution of 500 mg (1.72 mmol) 6-bromo-2-pyrrolidin-1-ylmethyl-quinoline (see 3.45b) in 10 mL acetic acid at RT. The mixture is stirred for 7 h at RT, again combined with 0.35 mL (3.46 mmol) borane-pyridine complex and stirred for another hour at RT. It is cooled to 0° C. and the solution is made basic with 8% NaOH solution. The aqueous phase is extracted with EtOAc and the solvent is eliminated i.vac. The residue is taken up with water and acidified with 12% HCl. The aqueous phase is extracted with EtOAc and then made basic with 20% NaOH solution while cooling with ice. The aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Aufarbeitung

  1. stirringstirred for another hour at RT
  2. temperatureIt is cooled to 0° C.
  3. extractionThe aqueous phase is extracted with EtOAc
  4. extractionThe aqueous phase is extracted with EtOAc
  5. temperaturewhile cooling with ice
  6. extractionThe aqueous phase is extracted with EtOAc
  7. dry with materialThe organic phase is dried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-10f61431b36d4f5f917a4aa83aa01a03
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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