Potassium Carbonate → 1-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol

HRID 403596

Reaktionsgleichung

Reaktionsgleichung von HRID 403596
[Si:1]([O:8][C:9]([CH3:14])([CH3:13])[C@@H:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[CH2:16][CH2:17][C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:22])[CH2:19][CH:20]=[CH2:21].C([O-])([O-])=O.[K+].[K+]>CC#N>[Si:1]([O:8][C:9]([CH3:13])([CH3:14])[C@@H:10]([NH:12][CH2:16][CH2:17][C:18]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([OH:22])[CH2:19][CH:20]=[CH2:21])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 159334751-Chloro-3-phenylhex-5-en-3-olHCID 58485259(S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine

Produkt 1

HCID 584852601-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-olAusbeute 3,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine (6 g, 27.6 mmol), 1-chloro-3-phenylhex-5-en-3-ol (4.83 g, 23 mmol) and K2CO3 (15 g, 100 mmol) in CH3CN (100 mL) was stirred and heated to reflux overnight. The solid was filtered, and the filtrate was concentrated to give the crude product which was purified by column chromatography to afford 1-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol (300 mg, 3%). 1H NMR (CDCl3): 0.00 (s, 6H), 0.73 (s, 9H), 1.02 (s, 3H), 1.12 (d, 3H), 1.21 (s, 3H), 1.92 (m, 2H), 2.30 (m, 4H), 2.49 (m, 3H), 2.96 (m, 2H), 4.92 (m, 3H), 5.45 (m, 2H), 7.11 (m, 1H), 7.21 (m, 2H), 7.26 (m, 2H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bb3c184400d74032900e677a39c26619
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748444B2

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