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6-(2,2,2-Trifluoroethoxy)pyridin-3-amine → 8-Hydroxy-2-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-aza-spiro[4.5]decan-1-one

HRID 2092663
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Reaktionsgleichung

Reaktionsgleichung von HRID 2092663
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.C([O:16][C:17]([C:19]1([CH2:26][CH2:27]OC)[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1)=O)C.[Cl-].C[Al+]C>C1(C)C=CC=CC=1>[OH:25][CH:22]1[CH2:23][CH2:24][C:19]2([C:17](=[O:16])[N:11]([C:8]3[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:12])[F:13])=[CH:6][CH:7]=3)[CH2:27][CH2:26]2)[CH2:20][CH2:21]1
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Komponenten

5

Edukt 3

HCID 5431566-(2,2,2-Trifluoroethoxy)pyridin-3-amineHCID 16686359Dimethylalumanylium chlorideHCID 582299764-Hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester

Produkt 1

HCID 665801358-Hydroxy-2-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-aza-spiro[4.5]decan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylamine (5.11 g, obtained in example 108, step 2) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (5.10 g, obtained in example 2, step 3) in toluene (160 mL). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (1M in hexane, 66.4 mL) was added dropwise over a period of 30 minutes. The reaction mixture was heated to reflux for 2 hours and then at 95° C. for 16 hours. The mixture was cooled, poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as an inseparable mixture of cis and trans diastereomeres as a brown oil (9.56 g, 100%). This mixture was used without further purification. MS (m/e): 345.1 [MH+].

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. waitat 95° C. for 16 hours
  4. temperatureThe mixture was cooled
  5. extractionextracted two times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f65bdc565ad849e58f3d224664de282f
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08440710B2

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