Sodium hydride → 3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine

HRID 617327

Reaktionsgleichung

Reaktionsgleichung von HRID 617327
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>CN(C=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27366983-Chloro-5-(trifluoromethyl)pyridineHCID 11007868((2R)-1-methylpyrrolidin-2-yl)methanol

Produkt 1

HCID 544356083-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-1-methyl-2-pyrrolidinemethanol (Aldrich Chemical Co.) was dissolved in 8 mL of DMF and stirred under N2, then 240 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 363 mg of 3-chloro-5-trifluoromethylpyridine (2.0 mmol) was added. The reaction mixture was stirred at 50° C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel, eluting with 2:1 ethyl acetate:hexane to give 336 mg of the title product. MS (DCI/NH3) m/e: 261 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.50 (d, J=0.6 Hz, 1H), 8.49 (d, J=3.0 Hz, 1H), 7.41 (dd, J=0.6, 3.0 Hz, 1H), 4.12-3.96 (m, 2H), 3.21-3.10 (m, 1H), 2.80-2.65 (m, 1H), 2.51 (s, 3H), 2.44-2.30 (m, 1H), 2.13-1.73 (m, 4H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred fifteen minutes
  2. stirringThe reaction mixture was stirred at 50° C. for 16 hours
  3. customThe volatiles were removed under vacuum
  4. customthe residue was purified by chromatography on silica gel
  5. washeluting with 2:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8bc050565f9344b79fb078141c72d6cb
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948793

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