Ammonium Chloride → tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 549941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549941
[Cl-].[C:2]1([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH:38]([C:40]1[N:41]=[C:42]([CH:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]2)[S:43][CH:44]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:2]1(/[CH:12]=[CH:38]\[C:40]2[N:41]=[C:42]([CH:45]3[CH2:46][CH2:47][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:49][CH2:50]3)[S:43][CH:44]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 2734113(1-Naphthylmethyl)triphenylphosphonium chlorideHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 67156180tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under argon, (1-naphthylmethyl)triphenylphosphonium chloride (2.96 g) is dissolved in 20 ml of tetrahydrofuran and cooled to 0° C., and potassium tert.-butoxide (757 mg) is added, whereupon the colour of the solution changes to dark-red. After 10 min of stirring, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.00 g) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.2 g, Z isomer).

Aufarbeitung

  1. stirringThe mixture is stirred at 0° C. for another 30 min
  2. temperatureslowly warmed to room temperature
  3. waitAfter a further 20 min
  4. customthe aqueous phase is separated off
  5. extractionAfter extraction of the aqueous phase with ethyl acetate
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customAfter chromatographic purification

Quellen und Nachweise

ORD-Eintrag
ord-0d049a1637d04d5aaeef52b4dda90224
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943774B2

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