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Ethyl Acetate → 1h-Indazole-6-methanamine,1-(tetrahydro-2h-pyran-2-yl)-

HRID 1263441
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1263441
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([CH2:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1)=[N+]=[N-].[OH-].[Na+].C(OCC)(=O)C>C1COCC1>[NH2:7][CH2:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 186161896-(Azidomethyl)-1-(2-tetrahydropyranyl)indazoleHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 186162001h-Indazole-6-methanamine,1-(tetrahydro-2h-pyran-2-yl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of LiAlH4 (9 mL, 9 mmol, 1.0 M) in THF was added dropwise to a yellow solution of 6-(azidomethyl)-1-(2-tetrahydropyranyl)indazole (2.4 g, 9 mmol) (101) in THF (30 mL) at 0° C. The addition time was 10 minutes, and gas came out. After stirring at 0° C. for 1 hour, NaOH (1.0 m, 1.5 mL) was added. The reaction mixture was allowed to warm to room temperature. Ethyl acetate (100 mL) was added, and the suspension was filtered through (Celite). The filter cake was washed with an addition portion of ethyl acetate (40 mL). Combined organic layers were evaporated under vacuum to five essentially pure amine (2.1 g, 97%). MS (electrospray) 232.5 (M+1); 1H NMR (CDCl3) δ1.67 (m, 3H), 2.01 (m, 2H), 2.48 (m, 1H), 3.85 (m, 1H), 3.94 (m, 1H), 5.75 (d, 1H, J=9.4 Hz), 7.14 (d, 1H, J=8.4 Hz), 7.62 (s, 1H), 7.62 (d, 1H, J=8.4 Hz), 7.93 (s, 1H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. filtrationthe suspension was filtered through (Celite)
  3. washThe filter cake was washed with an addition portion of ethyl acetate (40 mL)
  4. customCombined organic layers were evaporated under vacuum to five essentially pure amine (2.1 g, 97%)

Quellen und Nachweise

ORD-Eintrag
ord-82ec485aaffa4b7db2bf75d48e872290
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06541467B1

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