Potassium Hydroxide → 5-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamide

HRID 450934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450934
[OH-:1].[K+].[CH3:3][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:22])[CH2:5][CH2:6][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9]>CC(O)(CC)CC>[CH3:22][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:3])[CH2:5][CH2:6][C:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH2:9])=[O:1]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 547579545-Methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanenitrile

Produkt 1

HCID 160651355-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64933-methyl-3-PentanolLösungsmittel

Versuchsvorschrift

Potassium hydroxide (5.10 g, 91.98 mmol) was added to a solution of the product of example 1 (1.95 g, 4.60 mmol) in 3-methyl-3-pentanol (40 mL) and the mixture was heated under reflux for 24 hours. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between ethyl acetate (70 mL) and water (40 mL). The aqueous layer was separated, extracted with ethyl acetate (50 mL) and the combined organic solution was dried over sodium sulfate and concentrated in vacuo. The residue was then re-crystallised from hexane/ethyl acetate and dried under vacuum for 18 hours to afford the title compound as a white solid in 82% yield, 1.66 g.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (70 mL) and water (40 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (50 mL)
  7. dry with materialthe combined organic solution was dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was then re-crystallised from hexane/ethyl acetate
  10. customdried under vacuum for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-d0fcd75edd6e46a3bdebaddf135e138b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486992B2

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