Hydrochloric Acid → (3s)-3-(Tert-butyldimethylsiloxy)-5-phenyl-1-pentyne

HRID 593409Notizen

Reaktionsgleichung

N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[C:14]1([CH2:20][CH2:21][C@H:22]([OH:25])[C:23]#[CH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(Cl)Cl>[C:6]([Si:10]([CH3:12])([CH3:11])[O:25][C@@H:22]([CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:23]#[CH:24])([CH3:9])([CH3:8])[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Following a procedure of Noyori (Suzuki, M. et al., J. Med. Chem. 41, 3084-3090 (1998)); Imidazole (919.1 mg, 13.5 mmol, 1.8 eq.) and t-butylchlorodimethylsilane (1.35 g, 9.0 mmol) were added to a solution of (S)-5-phenylpent-1-yn-3-ol 86 (1.2 g, 7.5 mmol, 1 eq.) in CH2Cl2 (18 ml), cooled to 0° C. The reaction mixture was then stirred at room temperature for 14 h before being poured into 1 M HCl (50 ml). The mixture was extracted with 40/60 petroleum ether (3×50 ml). The combined organic phases were washed with brine (50 ml) before being dried (MgSO4), filtered and concentrated to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (99:1), giving the title product 88 as a clear, colourless oil (1.77 g, 86%). Analytical data consistent with the literature (Kiyotsuka, Y. et al., Org. Lett. 10, 1719-1722 (2008); Sato, F. et al., EP 1211241 A1, Taisho Pharmaceutical co., LTD (2002)).

Aufarbeitung

extractionThe mixture was extracted with 40/60 petroleum ether (3×50 ml)
washThe combined organic phases were washed with brine (50 ml)
dry with materialbefore being dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give the crude product
customThis was purified by column chromatography on silica
washeluting with petrol/Et2O (99:1)

Quellen und Nachweise

ORD-Eintrag: ord-7a5b4608b20442688372341863920dc2
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242954B2

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