Nitrogen → tert-Butyl 4-hydroxy-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

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Reaktionsgleichung

[OH:1][CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[NH:4][CH2:3]1.Br[C:21]1[CH2:25][O:24][C:23](=[O:26])[CH:22]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+].N#N.O>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[OH:1][CH:2]1[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:10][CH2:11]2)[C:5](=[O:19])[N:4]([C:21]2[CH2:25][O:24][C:23](=[O:26])[CH:22]=2)[CH2:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a round bottom flask was charged tert-butyl 4-hydroxy-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (300 mg, 1.11 mmol), 4-bromofuran-2(5H)-one (271 mg, 1.66 mmol), Pd(OAc)2 (24.9 mg, 0.111 mmol), Xantphos (96 mg, 0.166 mmol), and K2CO3 (307 mg, 2.22 mmol). The flask was sealed, vacuumed and back filled with N2 and filled with dioxane (4.5 mL) and H2O (60.0 μL, 3.33 mmol). The reaction mixture was heated at 90° C. overnight, then filtered through CELITE®, and evaporated to give the crude product, which was purified by column chromatography (0-10% MeOH/DCM) to give the title compound. LC/MS: [(M+1)]+=353

Aufarbeitung

customThe flask was sealed
filtrationfiltered through CELITE®
customevaporated
customto give the crude product, which
customwas purified by column chromatography (0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-a548a2cedf114cf8bb6d47113935959d
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08952166B2

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