Sodium borohydride → Ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate

HRID 2251538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251538
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)[CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:32][CH:33]=2)[CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:23])([CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 59643273Ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate

Produkt 1

HCID 69099388Ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoateAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (500 mg; 0.94 mmol) in 7 ml of methanol was cooled in an ice bath and treated with sodium borohydride (65 mg; 1.7 mmol) in small portions. After 30 minutes, the reaction mixture was concentrated and the residue partitioned between ethyl acetate and saturated brine. The organic phase was washed with water and the combined aqueous phases reextracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (5–50% gradient) afforded ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (450 mg; 85% yield).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated brine
  3. washThe organic phase was washed with water
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ceceb6dbe31453aa4d411f0b598b588
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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