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Sodium Hydroxide → (5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol

HRID 1662445
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1662445
[F:1][CH:2]([F:27])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:25])[CH3:24])[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:27][CH:2]([F:1])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:24])[CH3:25])[CH:8]=1
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705984Methyl 5'-(difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

Produkt 1

HCID 57706837(5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanolAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled solution of 66.51A (0.8631 g, 2.293 mmol) in dry THF (15.4 mL) at 0° C. was added LAH (1.0 M in THF) (4.6 mL, 4.6 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to a colorless oil as 66.51B (617.1 mg, 77% yield). MS ESI (pos.) m/e: 331.0 (M−H2O)+. Chiral separation of 66.51B was accomplished on a Chiracel-OD column (4% IPA in hexane) to provide 66.51C (peak 1) and 66.51D (peak 2). Both enantiomers were used to synthesize example compounds, and both enantiomers gave active compounds.

Aufarbeitung

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes)
  7. additionFractions containing the desired product

Quellen und Nachweise

ORD-Eintrag
ord-df3a9ffbb52243f8b881f169867fd54c
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030354B2

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