Acetic Acid → Ethyl 3-[2-(3-methoxypropoxy)-4'-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoate

HRID 1690613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690613
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](CCC(OCC)=O)[C:10]=2[O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:5][CH:4]=1)=O.[C:28]([OH:31])(=[O:30])[CH3:29].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:39].[Na+].[C:52](=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:27][O:26][CH2:25][CH2:24][CH2:23][O:22][C:10]1[CH:11]=[C:12]([CH2:52][CH2:29][C:28]([O:31][CH2:38][CH3:39])=[O:30])[CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:1][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:4][CH:5]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86633299Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl yl]propanoate

Produkt 1

HCID 66906385Ethyl 3-[2-(3-methoxypropoxy)-4'-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Ethyl 3-[4′-formyl-2-(3-methoxypropoxy)biphenyl yl]propanoate (1 g, 2.7 mmol) was dissolved in dichloroethane (20 mL). At 0° C., acetic acid (0.02 mL, 0.4 mmol) was added, followed by piperidine (0.25 g, 3 mmol) and sodium triacetoxyborohydride (0.86 g, 4 mmol) portionwise. The mixture was stirred at room temperature overnight. At, 0° C., saturated aqueous sodium bicarbonate solution was added. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine and water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 0.95 g (80%) of the desired product as a brown oil.

Aufarbeitung

  1. extractionThe aqueous layer was extracted three times with dichloromethane
  2. washThe combined organic layers were washed with brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-193e99effc42430ba6ebf51bbeb5bd79
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153647B2

Notizen zur Reaktion

Wird geladen…