Trimethylsilyl isocyanate → Benzyl 4-(5-allyl-2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxylate

HRID 20084

Reaktionsgleichung

C[Si]([N:5]=[C:6]=[O:7])(C)C.CO[C:10]([CH:12]([NH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1)[CH2:13][CH:14]=[CH2:15])=[O:11]>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:13]([CH:12]1[N:16]([CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])[CH2:21][CH2:22]2)[C:6](=[O:7])[NH:5][C:10]1=[O:11])[CH:14]=[CH2:15]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Trimethylsilyl isocyanate (1.66 g, 14.4 mmol) was added to a solution of benzyl 4-{[1-(methoxycarbonyl)but-3-en-1-yl]amino}piperidine-1-carboxylate (2.00 g, 5.77 mmol) and DMAP (71 mg, 0.57 mmol) in THF (30 mL) at room temperature. The reaction was heated at 50° C. for 48 h. The reaction was quenched with saturated aqueous sodium bicarbonate, extracted with methylene chloride (3×), dried over sodium sulfate, filtered and evaporated to give the crude product. The crude product was purified by chromatography (silica gel, 0 to 20% methanol in methylene chloride gradient elution), which gave the title compound (1.66 g). MS 358.2 (M+1).

Aufarbeitung

customThe reaction was quenched with saturated aqueous sodium bicarbonate
extractionextracted with methylene chloride (3×)
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customto give the crude product
customThe crude product was purified by chromatography (silica gel, 0 to 20% methanol in methylene chloride gradient elution), which

Quellen und Nachweise

ORD-Eintrag: ord-8d93a0870f3843e58d13c4eb51b91213
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745427B2

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