[2-(t-Butoxycarbonylaminomethyl)-1,4-cyclohexadienyl]acetic acid → [2-(N-t-Butoxycarbonylaminomethyl)-1-cyclohexen-1-yl]acetic acid

HRID 427003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427003
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH2:15][CH:14]=[CH:13][CH2:12][C:11]=1[CH2:16][C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[OH-].[NH4+].[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=1[CH2:16][C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 15918136[2-(t-Butoxycarbonylaminomethyl)-1,4-cyclohexadienyl]acetic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 15918137[2-(N-t-Butoxycarbonylaminomethyl)-1-cyclohexen-1-yl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

A solution of α-[2-(t-butoxycarbonylaminomethyl)-1,4-cyclohexadienyl]-acetic acid (1.33 g., 5 mmoles) in 3% ammonium hydroxide (10 ml.) was hydrogenated at 40 psi with palladium on charcoal (10%, 0.2 g.). A theoretical amount of hydrogen was taken up in 3 hours. The catalyst was removed and the filtrate was acidified to pH 2 with dil. HCl and extracted with ethyl acetate (2×50 ml.). The combined extracts were washed with water (20 ml.), dried with Na2SO4 and evaporated under reduced pressure to afford an oil (1.34 g.) which solidified on standing for several days. Recrystallization from n-hexane - ethyl acetate gave 1.2 g. title product as colorless prisms melting at 118°-119° C.

Aufarbeitung

  1. customThe catalyst was removed
  2. extractionextracted with ethyl acetate (2×50 ml.)
  3. washThe combined extracts were washed with water (20 ml.)
  4. dry with materialdried with Na2SO4
  5. customevaporated under reduced pressure
  6. customto afford an oil (1.34 g.) which
  7. waiton standing for several days
  8. customRecrystallization from n-hexane - ethyl acetate
  9. customgave 1.2 g

Quellen und Nachweise

ORD-Eintrag
ord-93b72fad863a464bbe97303d89077afc
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172199

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