Propanal → tert-Butyl 2-(1-hydroxyprop-1-yl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

HRID 8750

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.[O:19]1C[CH2:22][CH2:21][CH2:20]1.C([N-]C(C)C)(C)C.[Li+].C(=O)CC.[Cl-].[NH4+]>C(OCC)C>[OH:19][CH:20]([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])[CH2:21][CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 30 min at −78° C. before adding propionaldehyde (2.6 mL, 36 mmol). After 5 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (4.75 g).

Aufarbeitung

customby evaporating with toluene (10 mL) three times in vacuo
dissolutiondissolved in tetrahydrofuran (100 mL)
waitAfter 5 min
extractionextracted three times with diethyl ether
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-f4d34c0f487347f9a801ff3387bd1e3d
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091211B2

Verknüpfte Notizen

Wird geladen…