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

HRID 426888Notes

Reaction equation

HRID 426888 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

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.

Workup

  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
  9. customethyl acetate gave 1.2 g

Sources & evidence

ORD record
ord-a644c4ce791247da9d9a00f8118980fc
Source dataset
uspto-grants-1979_10
Patent number
US04171439

Reaction notes

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