Dimethylformamide → Tert-butyl 5-formyl-6-azaspiro[2.5]octane-6-carboxylate

HRID 536579

Reaktionsgleichung

[CH2:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.CN(C)CCN(C)C.CCCCCC.CN(C)[CH:32]=[O:33].[NH4+].[Cl-]>CCOCC>[CH:32]([CH:7]1[N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][C:3]2([CH2:2][CH2:1]2)[CH2:8]1)=[O:33]

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

tert-butyl 6-azaspiro[2.5]octane-6-carboxylate (Intermediate 2, 1 g, 4.73 mmol) dissolved in 20 ml of Et2O was cooled to −60° C., then N,N,N′,N′-tetramethyl ethylendiamine (0.71 ml, 4.73 mmol) and secBuLi 1.4M in hexane (4.05 ml, 5.68 mmol) were added. After 10 minutes at −60° C., the temperature was raised to −20° C. for 30 minutes, then the reaction was cooled to −78° C. and dimethylformamide (0.55 ml, 7.09 mmol, dissolved in 5 ml of Et2O) was added. After 30 minutes a saturated aqueous solution of NH4Cl (8 ml) was slowly added, then reaction was allowed to reach room temperature. Reaction was extracted with Et2O (3×50 ml), the organic solvent was dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether/ethylacetate from 95/5 to 85/15). (±) tert-butyl 5-formyl-6-azaspiro[2.5]octane-6-carboxylate was obtained as light yellow solid (400 mg).

Aufarbeitung

temperaturethe temperature was raised to −20° C. for 30 minutes
temperaturethe reaction was cooled to −78° C.
customreaction
customto reach room temperature
customReaction
extractionwas extracted with Et2O (3×50 ml)
dry with materialthe organic solvent was dried (Na2SO4)
customevaporated
customto obtain a crude that
customwas purified by silica gel chromatography (petroleum ether/ethylacetate from 95/5 to 85/15)

Quellen und Nachweise

ORD-Eintrag: ord-2112b7de8e8942758b2b053a5b22a2a8
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08859608B2

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