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Aluminium lithium hydride → HCID 86684769, Verbindung

HRID 579160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579160
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@H:11]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:12](=[O:17])N(OC)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@H:11]([CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH:12]=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydride2×HCID 86684768HCID 86684768, Verbindung

Produkt 1

HCID 86684769HCID 86684769, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of [(R)-Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid benzyl ester (27 g, 82 mmol) in THF (400 mL) at −20° C. was slowly added LiAlH4 (4.06 g, 106 mmol, 1.3 equiv). LiAlH4 was freshly ground from pellet purchased from Aldrich. During addition, the internal temperature was carefully monitored and did not rise above 0° C. After addition the mixture was stirred at 0° C. and the reaction was monitored by TLC and LCMS. After 1 hour, the reaction solution was cooled at −10° C. and quenched by slow addition of sat. aq. KHSO4 solution until pH=5. The mixture was partitioned between water and EtOAc. The phases were separated and the organic layer was concentrated. The residue was dissolved in EtOAc and the solution was washed with water, brine, dried over Na2SO4 and concentrated to give product ((R)-1-Cyclohexyl-2-oxo-ethyl)-carbamic acid benzyl ester 22 g (99%). The material was continued to next step with no further purification.

Aufarbeitung

  1. customat −20° C.
  2. additionDuring addition
  3. customdid not rise above 0° C
  4. additionAfter addition the mixture
  5. temperaturethe reaction solution was cooled at −10° C.
  6. customquenched by slow addition of sat. aq. KHSO4 solution until pH=5
  7. customThe mixture was partitioned between water and EtOAc
  8. customThe phases were separated
  9. concentrationthe organic layer was concentrated
  10. dissolutionThe residue was dissolved in EtOAc
  11. washthe solution was washed with water, brine
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ad54c1f563c247549f07b896c7a529f7
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040690B2

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