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Ethyl Acetate → Ethyl [3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-4-hydroxy-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

HRID 1946481
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1946481
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]3[C:30](=[O:35])[CH2:31][CH2:32][CH2:33][CH2:34][C:28]=3[N:27]=[C:26]2[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]2[C:29]3[C:30]([CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3])([OH:35])[CH2:31][CH2:32][CH2:33][CH2:34][C:28]=3[N:27]=[C:26]2[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:22][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 584602383-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-one

Produkt 1

HCID 58460200Ethyl [3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-4-hydroxy-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ethyl acetate (0.695 mL) was added dropwise to a stirred solution of LiHMDS, 1M in THF (7.10 ml) cooled to −78° C. under nitrogen atmosphere. The mixture was stirred at −78° C. for 30 minutes. Intermediate 14 was dissolved in THF (3 ml) and added dropwise. The RM was stirred at −78° C. under nitrogen for 2 hours. An excess of sat. NH4Cl aq. sol. added and the resulting suspension warmed up to room temp and extracted with EtOAc (100 ml). The phases were separated and the aqueous layer was again extracted with EtOAc (50 ml), the phases were separated. The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a Dichloromethane:Ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (420 mg). LC/MS MH+419, Rt 1.93 min (5 minute run).

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe RM was stirred at −78° C. under nitrogen for 2 hours
  3. temperaturethe resulting suspension warmed up to room temp
  4. extractionextracted with EtOAc (100 ml)
  5. customThe phases were separated
  6. extractionthe aqueous layer was again extracted with EtOAc (50 ml)
  7. customthe phases were separated
  8. customdried (hydrophobic frit)
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified on silica using a Dichloromethane
  11. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-235094cf5cb0411b840c99dd79e3fd38
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399444B2

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