Ethyl Acetate → 8-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

HRID 8748

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([O:16]C)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.C([N-]C(C)C)(C)C.[Li+].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH3:24][O:23][C:21]([CH:20]1[CH2:19][CH2:18][C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[C:14]1=[O:16])=[O:22]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate (20.1 g, 0.058 mol) from Step E in tetrahydrofuran (600 mL) at −78° C. was added lithium diisopropylamide mono(tetrahydrofuran) (47 mL, 0.070 mol, 1.5M solution in cyclohexanes). The reaction mixture was stirred at −78° C. for 25 min. Thin layer chromatography (tlc) analysis (50% ethyl acetate in hexanes) showed that starting material remained. Additional lithium diisopropylamide mono(tetrahydrofuran) (31 mL) was added and the reaction mixture was stirred for 20 min. The reaction mixture was poured into saturated ammonium chloride and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated to afford the title compound (19.9 g) which was taken on to the next step without further purification.

Aufarbeitung

stirringthe reaction mixture was stirred for 20 min
extractionextracted three times with diethyl ether
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-2199290325e045e6997c103221fdd023
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091211B2

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