3-(Pyridin-3-yl)propanal → (+/-)-1-[1-(Biphenyl-4-yloxy)-cyclopropyl]-3-pyridin-3-yl-propan-1-ol

HRID 379975

Reaktionsgleichung

Reaktionsgleichung von HRID 379975
[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].C1(S[C:19]2([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:21][CH2:20]2)C=CC=CC=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][CH2:42][CH:43]=[O:44])[CH:36]=1>O1CCCC1>[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([O:22][C:19]2([CH:43]([OH:44])[CH2:42][CH2:41][C:37]3[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=3)[CH2:20][CH2:21]2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 111054123-(Pyridin-3-yl)propanalHCID 11768624Lithium naphthalenideHCID 183675314-(1-Phenylsulfanyl-cyclopropoxy)biphenyl

Produkt 1

HCID 18367552(+/-)-1-[1-(Biphenyl-4-yloxy)-cyclopropyl]-3-pyridin-3-yl-propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium naphthalenide (0.625M, 7.4 ml; prepared by adding equimolar quantities of naphthalene and lithium metal to tetrahydrofuran, under nitrogen, and stirring at room temperature overnight) was added slowly to a stirred solution of 4-(1-phenylsulfanyl-cyclopropoxy)biphenyl (0.7 g) in dry tetrahydrofuran at −78° C., under nitrogen, and then stirred at this temperature for 15 minutes. To this was added a solution of 3-pyridinepropanal (0.3 g, prepared according to the method of Example 3 of International Patent Application No. WO-A-92/19593) in dry tetrahydrofuran (15 ml), and the stirring was continued at −78° C. for 5 minutes, then allowed to warm up to room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution, and extracted into diethyl ether (3×30 ml). The combined extracts were washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a pale yellow gum, which was further purified by reverse phase HPLC to give the title compound as a pale yellow gum (0.11 g).

Aufarbeitung

  1. customprepared
  2. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted into diethyl ether (3×30 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a pale yellow gum, which
  9. customwas further purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e76b78f81fee448a8a9e190f591853dd
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300352B1

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