Tetrabutylammonium Fluoride → 2-amino-5-(4-hydroxycyclohexyl)-N,N-dimethylbenzamide

HRID 1947971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947971
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH:16]([O:19][Si](C(C)(C)C)(C)C)[CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 672546822-amino-5-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-N,N-dimethylbenzamide2×

Produkt 1

HCID 672547852-amino-5-(4-hydroxycyclohexyl)-N,N-dimethylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2-amino-5-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-N,N-dimethylbenzamide (Compound 173B, 0.320 g, 0.850 mmol) in THF (2 mL) was charged with 1.0 M of tetra-n-butylammonium fluoride in THF (8.50 mL) and stirred at rt over night. The reaction mixture was partitioned between EtOAc and water and separated. The aqueous was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The compound was purified on an Isco Combiflash unit eluting with 75 to 100% EtOAc in heptane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 6.91-6.97 (m, 1H), 6.80-6.85 (m, 1H), 6.59-6.64 (m, 1H), 4.94 (s, 2H), 4.30 (d, J=3.79 Hz, 1H), 2.91 (s, 6H), 2.24-2.39 (m, 1H), 1.62-1.80 (m, 4H), 1.34-1.54 (m, 4H), 1.20-1.32 (m, 1H); MS (ES+): m/z: 263.15 [MH+]. HPLC: tR=2.84 min (Micromass ZQ3: polar—3 min).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customseparated
  3. extractionThe aqueous was extracted with EtOAc (3×)
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound was purified on an Isco Combiflash unit
  9. washeluting with 75 to 100% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-cae72799e4714235b1c850aac230f6dd
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399433B2

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