Acetic Acid → tert-Butyl 2-[3-[N-(3-hydroxypropyl)aminomethyl]phenoxy]butyrate

HRID 350847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350847
[CH:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([CH2:15][CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[OH:24][CH2:23][CH2:22][CH2:21][NH:20][CH2:1][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([CH2:15][CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21090531Tert-butyl 2-(3-formylphenoxy)butyrate

Produkt 1

HCID 21090533tert-Butyl 2-[3-[N-(3-hydroxypropyl)aminomethyl]phenoxy]butyrateAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(3-formylphenoxy)butyrate (105.1 mg, 0.42 mmol) was dissolved in chloroform (10 ml) at room temperature, and thereto were added 3-amino-1-propanol (0.04 ml, 0.47 mmol), sodium triacetoxyborohydride (134.6 mg, 0.63 mmol) and acetic acid (0.03 ml, 0.51 mmol) in sequential order at the same temperature, and then stirred at room temperature for 24 hours. The reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution and thereafter extracted by chloroform, to obtain an organic layer. The extracted organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressured. The resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained as a colorless oil (43.3 mg, 33.3%).

Aufarbeitung

  1. extractionextracted by chloroform
  2. customto obtain an organic layer
  3. washThe extracted organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressured
  6. customThe resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound

Quellen und Nachweise

ORD-Eintrag
ord-04c9ac37f7034908adec7a5aa6165d83
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183295B2

Notizen zur Reaktion

Wird geladen…