Trifluoroacetic acid → tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 276886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276886
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 226295651-Boc-4-(2-methoxyphenyl)-4-hydroxypiperidine

Produkt 1

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-t-Butoxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine (230 mg, 0.75 mmol) was dissolved in methylene chloride (10 ml). Thereto was added trifluoroacetic acid (0.20 ml, 2.6 mmol) and the resulting solution was stirred at a room temperature for 2.5 hours. The reaction solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 150 mg of the aforementioned compound of interest (0.53 mmol, 71% in yield).

Aufarbeitung

  1. washThe reaction solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-33668dde66c5413ab0dfbec8f5ed6ed4
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355642B1

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