Hydrochloric Acid → {2-[3,5-Bis(trifluoromethyl)phenyl]ethyl}{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amine

HRID 17082

Reaktionsgleichung

Reaktionsgleichung von HRID 17082
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[C:28]2[CH:33]=[C:32]([CH:34]([CH3:36])[CH3:35])[CH:31]=[CH:30][C:29]=2[O:37][CH3:38])=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[OH-].[Na+]>C1COCC1>[F:1][C:2]([F:39])([F:40])[C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:19]=2[C:28]2[CH:33]=[C:32]([CH:34]([CH3:36])[CH3:35])[CH:31]=[CH:30][C:29]=2[O:37][CH3:38])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866153972-[3,5-bis(trifluoromethyl)phenyl]-N-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}acetamide

Produkt 1

HCID 86615398{2-[3,5-Bis(trifluoromethyl)phenyl]ethyl}{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-[3,5-bis(trifluoromethyl)phenyl]-N-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}acetamide (77.6 mg, 0.134 mmol) in THF (4.4 mL) was added BH3 (1.34 mL of a 1M solution in THF, 1.34 mmol). The reaction was stirred overnight at room temperature and then 1 N HCl (10 mL) was added. The mixture was stirred for 5 minutes and then adjusted to a slightly basic pH with 1 N NaOH. The mixture was then extracted with CH2Cl2 (4×20 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography with 25 to 40% EtOAc/hexanes gave {2-[3,5-bis(trifluoromethyl)phenyl]ethyl}{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amine. Rf=0.17 (25% EtOAc/hexanes). LCMS=564.3 (M+1)+. 1H NMR (CD2Cl2, 500 MHz) δ 7.75 (s, 1H), 7.73 (s, 1H), 7.64 (s, 2H), 7.53 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.24 (dd, J=8.2, 2.0 Hz, 1H), 6.98 (d, J=2.3 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 3.58-3.73 (m, 5H), 2.88 (m, 1H), 2.74-2.81 (m, 4H), 1.22 (d, J=6.9 Hz, 6H).

Aufarbeitung

  1. stirringThe mixture was stirred for 5 minutes
  2. extractionThe mixture was then extracted with CH2Cl2 (4×20 mL)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography with 25 to 40% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2017967f956d4581b0545448abddf988
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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