Acetic Acid → (R)-Quinuclidin-3-yl 2-(4-methylbenzylamino)-2-phenylacetate

HRID 77007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77007
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:19])[CH:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C1CCCCC1>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:19])[CH:11]([NH:18][CH2:20][C:21]1[CH:28]=[CH:27][C:24]([CH3:25])=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59401091(R)-quinuclidin-3-yl 2-amino-2-phenylacetate

Produkt 1

HCID 59401115(R)-Quinuclidin-3-yl 2-(4-methylbenzylamino)-2-phenylacetateAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

To a solution of amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (I76) (100 mg, 0.38 mmol) in dry THF (3.84 mL), are added 4-methylbenzaldehyde (68 mL, 0.57 mmol) and AcOH (0.5 mL, 8.73 mmol). The mixture is stirred at RT and sodium triacetoxyborohydride (163 mg, 0.77 mmol) is added. The reaction is stirred at RT for 1.5 hours then cyclohexane is added and the mixture is evaporated to dryness. The crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5) to obtain the title compound as a colorless oil (76 mg, 54% yield, mixture of diastereoisomers).

Aufarbeitung

  1. stirringThe reaction is stirred at RT for 1.5 hours
  2. customthe mixture is evaporated to dryness
  3. customThe crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-74b3e9a6b35b420ca4eddb16d9a94bcb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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