Boron trifluoride etherate → tert-Butyl 4-hydroxy-4-(3-phenylprop-2-ynyl)piperidine-1-carboxylate

HRID 1896010

Reaktionsgleichung

Reaktionsgleichung von HRID 1896010
B(F)(F)F.CCOCC.[Li+].[C-:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O:19]1[C:21]2([CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:20]1>C1COCC1>[OH:19][C:21]1([CH2:20][C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 3437284Lithium phenylacetylideHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Produkt 1

HCID 86627346tert-Butyl 4-hydroxy-4-(3-phenylprop-2-ynyl)piperidine-1-carboxylateAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

Boron trifluoride diethyl etherate (0.131 mL, 1.03 mmol) followed by lithium phenylacetylide (1M in THF, 1.03 mL, 1.03 mmol) was dropped into a solution of Compound 256a (200 mg, 0.938 mmol) in THF (5 mL) stirred at −75° C. under nitrogen atmosphere. Stirring and cooling were kept on for 2 h and after overnight stirring at r.t., the reaction mixture was quenched with water and EtOAc. The combined extracts were washed, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (EtOAc—Petroleum Ether 85:15) affording the title product (272 mg).

Aufarbeitung

  1. stirringStirring
  2. temperaturecooling
  3. stirringstirring at r.t.
  4. customthe reaction mixture was quenched with water and EtOAc
  5. washThe combined extracts were washed
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (EtOAc—Petroleum Ether 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-aad17222f93344df9a3fc42be36177bf
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518916B2

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