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

HRID 426888ノート

反応式

HRID 426888 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 14923Ammonium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a644c4ce791247da9d9a00f8118980fc
出典データセット
uspto-grants-1979_10
特許番号
US04171439

反応ノート

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