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Tert-butyl-(3-iodopropoxy)-dimethylsilane → 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one

HRID 579172
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579172
[CH:1]1([CH:7]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:11](=[O:22])[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.[C:28]([Si:32]([O:35][CH2:36][CH2:37][CH2:38]I)([CH3:34])[CH3:33])([CH3:31])([CH3:30])[CH3:29]>C1COCC1>[C:28]([Si:32]([CH3:34])([CH3:33])[O:35][CH2:36][CH2:37][CH2:38][CH:10]1[O:9][CH2:8][CH:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:11]1=[O:22])([CH3:31])([CH3:30])[CH3:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11022956Tert-butyl-(3-iodopropoxy)-dimethylsilaneHCID 666847235-Cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-oneHCID 178418339Butyllithium

Produkt 1

HCID 666846652-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one (700 mg, 2.3 mmol, 1.0 equiv) in THF (10.0 mL) at −78° C. was added n-BuLi (1.58 mL, 1.6 M in heptane, 2.54 mmol, 1.1 equiv). The resulting solution was stirred at −78° C. for 30 minutes, after which it was added a solution of tert-Butyl-(3-iodo-propoxy)-dimethyl-silane (693 mg, 2.3 mmol, 1.0 equiv) in THF (1.0 mL). The solution was stirred at −78° C. for 30 minutes and 2 hours at room temperature after which it was quenched by addition of sat. aq. NH4Cl solution. The mixture was extracted with EtOAc. The organic layer was combined, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 30% to give product 480 mg (yield 44%).

Aufarbeitung

  1. stirringThe solution was stirred at −78° C. for 30 minutes and 2 hours at room temperature after which it
  2. customwas quenched by addition of sat. aq. NH4Cl solution
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography, EtOAc/heptane 30%

Quellen und Nachweise

ORD-Eintrag
ord-162c6b4c046f4cf6965bc8bdc1fe3606
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040690B2

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