3,4-dihydro-2H-pyran → 5-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

HRID 1416356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416356
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:7]2.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[CH2:7]2

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 154910662-Trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol

Produkt 1

HCID 154342975-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3.7 g (15.9 mmol) of 5-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (Example 1) and 4.4 mL (47.7 mmol) 2,3-dihydropyrane were dissolved in dichloromethane and catalytic amount of p-toluenesulfonic acid monohydrate was added. After completion of the reaction (System A), the reaction mixture was diluted with dichloromethane, washed with water and aqueous sodium chloride. The solution was dried over Na2SO4, evaporated to dryness, and the product was purified by silicagel chromatography (System A). Yield 4.13 g, 79%. 1H NMR (CDCl3, 400 MHz): 7.16 (1H, m), 7.00 (1H, m), 6.77 (1H, m), 5.45 (1H, m), 4.79 (2H, ss), 3.8 (3H, m), 3.6 (1H, m), 2.9 (4H, m).

Aufarbeitung

  1. customAfter completion of the reaction (System A), the reaction mixture
  2. washwashed with water and aqueous sodium chloride
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated to dryness
  5. customthe product was purified by silicagel chromatography (System A)

Quellen und Nachweise

ORD-Eintrag
ord-b889aade26804b538c19425e381f7305
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912342

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