Diisopropylethylamine → [3-(t-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-carbamic acid t-butyl ester
Reaktionsgleichung
[CH3:1][C:2]([Si:5]([CH3:12])([CH3:11])[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1)([CH3:4])[CH3:3].C(N(CC)C(C)C)(C)C.[CH3:22][C:23]([O:26][C:27]([N:29]1C(C2C=CC(C#N)=CC=2)O1)=[O:28])([CH3:25])[CH3:24]>ClCCl>[C:23]([O:26][C:27](=[O:28])[NH:29][N:9]1[CH2:10][CH:7]([O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:12])[CH3:11])[CH2:8]1)([CH3:25])([CH3:24])[CH3:22]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-azetidine (300 mg, 1.6 mmol) was combined with dichloromethane (16 mL) to give a brown solution. N,N-Diisopropylethylamine (455 mg, 615 μl, 3.52 mmol) was added at 0° C. Subsequently 3-(4-cyanophenyl)-2-oxaziridinecarboxylic acid 1,1-dimethylethyl ester (355 mg, 1.44 mmol) in dichloromethane (10 mL) was added during 25 min at 0° C. and the reaction mixture was stirred for 1 h at 0° C. Afterwards the reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 20 g, 0% to 40% ethyl acetate in n-heptane) to deliver an oil contaminated with 4-cyano-benzaldehyde. This material was purified by a second chromatography (aminophase 12 g, ethyl acetate/n-heptane 1/1) to give the title compound (320 mg, 67%) as white waxy solid; GC-MS (EI) 302.0 (M)+.
Aufarbeitung
- customto give a brown solution
- concentrationAfterwards the reaction mixture was concentrated in vacuo
- customthe residue was purified by flash chromatography (silica gel, 20 g, 0% to 40% ethyl acetate in n-heptane)
- customThis material was purified by a second chromatography (aminophase 12 g, ethyl acetate/n-heptane 1/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-b3c05a07072e40bbad363c06f97491b9
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08648099B2
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