Hydrochloric Acid → tert-Butyl 2-(hydroxymethyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

HRID 8753

Reaktionsgleichung

[O:1]=[C: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)[CH2:5][CH2:4][CH2:3]1.[CH:19](OCC)=[O:20].CC(C)([O-])C.[K+].Cl>C(OCC)C>[OH:20][CH2:19][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:2]1=[O:1]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min.

Aufarbeitung

customby evaporating with toluene (10 mL) three times in vacuo
dissolutiondissolved in methyl-tert-butyl ether (5 mL)
extractionextracted three times with diethyl ether
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto afford 0.575 g
customThe residue was purified by flash chromatography
washeluting with 45% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-01aabc2e796f428ba758c5068521a6d6
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091211B2

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