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Benzyltriphenylphosphonium bromide → trans-N-Boc-2-methyl-6-(2-phenylethenyl)piperidine

HRID 1919720
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1919720
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]CCCC.[C:33]([N:40]1[C@@H:45]([CH:46]=O)[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH3:48])([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CCOC(C)=O.CCCCCC>C1COCC1.O>[C:33]([N:40]1[C@@H:41]([CH:48]=[CH:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:42][CH2:43][CH2:44][C@@H:45]1[CH3:46])([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 2734970Benzyltriphenylphosphonium bromideHCID 10878893tert-butyl (2R,6S)-2-formyl-6-methylpiperidine-1-carboxylateHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Produkt 1

HCID 67499694trans-N-Boc-2-methyl-6-(2-phenylethenyl)piperidineAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A suspension of benzyltriphenylphosphonium bromide (10.3 g, 26.5 mmol) in 54 mL of THF was cooled to −30° C. and treated with n-BuLi (11.2 mL, 26.88 mmol) dropwise. The deep red solution was slowly warmed to 0° C., stirred for 30 min, and then cooled to −78° C. The ylide was treated with a solution of trans-N-Boc-2-Methyl-6-Piperidinecarboxaldehyde (4.00 g, 18.93 mmol) in 6 mL of THF, and the mixture was slowly warmed to room temperature. The mixture was diluted with water, and the organic layer was separated. The aqueous layer was extracted with ether and the combined extracts were dried over K2CO3 and then concentrated to give a crude product as an oil. Chromatography on silica with 5% EtOAc/hexane afforded 3.8 g (66%) of the product which was homogeneous by TLC analysis. 1H NMR (250 MHz) δ 7.35-7.19 (m, 5H), 6.38-6.34 (m, 1H), 5.80-5.76 (m, 1H), 4.74-4.67, (m, 1H), 4.35-4.18 (m, 1H), 1.80-0.88 (m, 18H).

Aufarbeitung

  1. temperatureThe deep red solution was slowly warmed to 0° C.
  2. temperaturecooled to −78° C
  3. temperaturethe mixture was slowly warmed to room temperature
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with ether
  6. dry with materialthe combined extracts were dried over K2CO3
  7. concentrationconcentrated
  8. customto give a crude product as an oil

Quellen und Nachweise

ORD-Eintrag
ord-77be17e50abf46189bc493ba3ca24c56
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08168657B2

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