Benzaldehyde → Methyl 2-(benzylamino)-2-phenylacetate

HRID 1951574

Reaktionsgleichung

Reaktionsgleichung von HRID 1951574
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([NH:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 117324Methyl phenylglycineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 3699844Methyl 2-(benzylamino)-2-phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

to a mixture of benzaldehyde (3.06 ml, 30.3 mmol) and methyl 2-amino-2-phenylacetate 1a (4.552 g, 27.6 mmol) in 50 mL 1,2-dichloroethane was added sodium triacetoxyborohydride (14.6 g, 68.9 mmol) all at once. The reaction mixture was stirred at room temperature for several hours then poured into 100 mL saturated aqueous sodium bicarbonate solution. The biphase was vigorously stirred for 15 minutes then the organic separation dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless oil. The product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane. ESI+ m/z=256.1 [MH]+.

Aufarbeitung

  1. stirringThe biphase was vigorously stirred for 15 minutes
  2. customthe organic separation
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford a colorless oil
  7. customThe product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-faf6b9ad5d1e4cbd97e017ffbeac859c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404722B2

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