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Diisobutylaluminumhydride → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

HRID 1515655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1515655
C([O:3][C:4](=O)[C:5]([O:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[CH2:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[NH:15][C:12]2=[N:13][CH:14]=1)([CH3:7])[CH3:6])C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH:20]1([CH2:19][CH:18]([C:16]2[NH:15][C:12]3=[N:13][CH:14]=[C:9]([O:8][C:5]([CH3:6])([CH3:7])[CH2:4][OH:3])[CH:10]=[C:11]3[CH:17]=2)[C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1
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Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 583052662-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid ethyl ester

Produkt 1

HCID 532507462-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-olAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid ethyl ester (prepared as in Example 26, 300 mg, 0.6 mmol) in dry tetrahydrofuran (10 mL) at −78° C. was added diisobutylaluminum hydride (3.0 mL, 3.01 mmol). The mixture was then warmed to room temperature and stirred for 1 h. The reaction was quenched with a saturated aqueous potassium sodium tartrate solution at 0° C. After stirring at 0° C. for 30 min, the mixture was filtered and washed with tetrahydrofuran (100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (236 mg, 86.1%) as a white solid: LC/MS m/e calcd for C25H32N2O4S [M+H]+ 457.61, observed 457.1; 1H NMR (400 MHz, CD3OD) δ ppm 7.87-7.92 (m, 3H), 7.59-7.64 (m, 3H), 6.36 (s, 1H), 4.31 (t, J=7.8 Hz, 1H), 3.56 (s, 2H), 3.10 (s, 3H), 2.25-2.34 (m, 1H), 2.07-2.15 (m, 1H), 1.62-1.89 (m, 6H), 1.45-1.57 (m, 2H), 1.02-1.42 (m, 6H).

Aufarbeitung

  1. customThe reaction was quenched with a saturated aqueous potassium sodium tartrate solution at 0° C
  2. stirringAfter stirring at 0° C. for 30 min
  3. filtrationthe mixture was filtered
  4. washwashed with tetrahydrofuran (100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-af15b948a8a647e6ad697fa6f4d89ae9
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222416B2

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