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Triethylamine → (R)-{2-[3,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanol

HRID 1740101
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1740101
[CH2:1]([C:3]1[C:7]([CH2:8]O)=[C:6]([CH2:10][CH3:11])[N:5]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:4]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[OH:33][CH2:34][CH:35]1[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][NH:36]1>C(Cl)Cl.C(#N)C.CN(C)C=O.O>[CH2:1]([C:3]1[C:7]([CH2:8][N:36]2[C@@H:35]([CH2:34][OH:33])[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[C:6]([CH2:10][CH3:11])[N:5]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:4]=1)[CH3:2]
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Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanolHCID 218373233,5-Diethyl-1-(2,4,6-trimethylphenyl)pyrazole-4-methanol

Produkt 1

HCID 67553250(R)-{2-[3,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanolAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 272 mg (1,0 mmol) of 3,5-diethyl-1-(2,4,6-trimethylphenyl)pyrazole-4-methanol in 5 mL of methylene chloride cooled to 0° C. under dry nitrogen in a 25 mL 3-neck flask, was added to 0.2 mL (2.5 mmol) of triethylamine and 0.092 mL (2.0 mmol) of methanesulfonyl chloride. This mixture was stirred for 15 minutes at 0° C. and then 0.648 g (4.0 mmol) of (+)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline in 1 mL of 50:50 dimethylformamide acetonitrile was added. The reaction mixture was heated at reflux overnight whereupon no starting material was seen by TLC. The cooled reaction mixture was diluted with water and the product was extracted with ethyl acetate. After drying (brine wash, magnesium sulfate) and evaporation, the crude product was chromatographed on silica gel, eluting with 10:1 and 5:1 hexane/ethyl acetate to give 184 mg (44%) of the desired product. 1H-NMR (CDCl3):0.80 (3H, t, J=7), 1.18 (3H, t, J=7), 1.92 (6H, s), 2.21 (2H, q, J=7), 2.28 (3H, s), 2.55 (2H, q, J=7), 2.97 (2H, d of d, J=7), 3.25 (1H, m), 3.50-3.66 (5H, m), 3.80 (2H, d, J=12), 6.82-7.16 (6H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight whereupon no starting material
  3. customThe cooled reaction mixture
  4. extractionthe product was extracted with ethyl acetate
  5. customAfter drying
  6. wash(brine wash, magnesium sulfate) and evaporation
  7. customthe crude product was chromatographed on silica gel
  8. washeluting with 10:1 and 5:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-31ac6f64ce924e1683bcba94e1e69668
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05968944

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