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Benzaldehyde → Benzyl-(3-methyl-2-phenyl-butyl)-amine

HRID 1698306
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1698306
[CH3:1][CH:2]([CH3:12])[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][NH2:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH2:13]([NH:5][CH2:4][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]([CH3:12])[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 240Benzaldehyde2×HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 98802173-Methyl-2-phenylbutan-1-amine

Produkt 1

HCID 67273216Benzyl-(3-methyl-2-phenyl-butyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol), benzaldehyde (271 μL, 2.66 mmol) and CH2Cl2 (50 mL) is stirred for 20 min at RT. NaBH(OAc)3 (840 mg, 3.96 mmol) and acetic acid (154 μL, 2.69 mmol) are added. After 2 h the same amounts as indicated above of benzaldehyde, NaBH(OAc)3 and acetic acid are added once again. This procedure is repeated after 4 h. After stirring for 16 h at RT, saturated NaHCO3 solution is added, the CH2Cl2 layer is removed and the aqueous phase is extracted twice with fresh CH2Cl2. The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated to afford the title compound as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min.

Aufarbeitung

  1. additionare added once again
  2. waitThis procedure is repeated after 4 h
  3. stirringAfter stirring for 16 h at RT
  4. customthe CH2Cl2 layer is removed
  5. extractionthe aqueous phase is extracted twice with fresh CH2Cl2
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. customevaporated in vacuo
  8. customthe residue is purified by flash chromatography (hexane/ethyl acetate)
  9. customThe combined pure fractions are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-02b6cf03594a427abda63cc9c81bd0bf
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163773B2

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