Acetic Acid → 3-Bromo-4-(pyrrolidin-1-ylmethyl)pyridine

HRID 2383920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383920
C(O)(=O)C.[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH:12]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCCCCC.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH2:12][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 596361363-Bromo-4-(pyrrolidin-1-ylmethyl)pyridineAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetic acid (0.1 mL) was added to a stirred solution of 3-bromo-pyridine-4-carbaldehyde (220 mg, 1.18 mmol) and pyrrolidine (0.11 mL, 1.34 mmol) in DCE (15 mL) under nitrogen atmosphere and stirred at room temperature for 2 hours. This was followed by addition of NaBH(OAc)3 (342 mg, 1.612 mmol) at 0° C. over a period of 10 minutes. The resulting reaction mass was stirred for 12 hours at room temperature. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was washed with NaHCO3 solution and extracted using ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to afford 275 mg of the product (98.2% yield).

Aufarbeitung

  1. customThe resulting reaction mass
  2. stirringwas stirred for 12 hours at room temperature
  3. washThe reaction mixture was washed with NaHCO3 solution
  4. extractionextracted
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ba2945e817e84d48a68db6216bdc198c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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