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

HRID 1843968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843968
C(O)(=O)C.[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCCCCC.C(OC(=O)C)C>[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH2:8][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 96,52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Catalytic amount of acetic acid (0.3 mL) was added to a mixture of 3-bromoisonicotinaldehyde (200 mg, 1.075 mmol) and pyrrolidine (0.12 mL, 1.34 mmol) in DCE (20 mL) under nitrogen atmosphere and the resulting mixture was stirred at room temperature for 2.3 hours. This was followed by the addition of sodium triacetoxy-borohydride (342 mg, 1.612 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was washed with NaHCO3 solution and separated the layers. The organic layer was dried over Na2SO4 and concentrated to afford 250 mg of the product (96.52% yield).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washThe reaction mixture was washed with NaHCO3 solution
  3. customseparated the layers
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e993270ffbbd4f8f8c0f75807bf2bc26
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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