1,4-Cyclohexadiene → 2-[4-(2-Methyl-oxazol-4-yl)-phenoxy]-ethylamine

HRID 49393

反応式

HRID 49393 の反応式
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([CH3:25])[O:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.C1CC=CCC=1>>[CH3:25][C:22]1[O:23][CH:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:15][CH:16]=2)[N:21]=1

参加物

3

反応物 2

HCID 123431,4-CyclohexadieneHCID 20587951Benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl]-carbamate

生成物 1

HCID 98132202-[4-(2-Methyl-oxazol-4-yl)-phenoxy]-ethylamine収率 100.9%

実験手順

A round-bottomed flask containing benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl}-carbamate (788 mg, 2.07 mmol) was purged with nitrogen, and 10% Pd/C (200 mg, 20 wt %), ethyl acetate (15 ml), and methanol (5 ml) were added. 1,4-cyclohexadiene (0.90 ml, 9.60 mmol) was then added to the mixture, and the solution was allowed to stir at room temperature for about one hour. The reaction mixture was then filtered through a pad of diatomaceous earth and the filter cake was washed with methanol. The filtrate was concentrated in vacuo and the residue purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride) to afford 456 mg (89% yield) of the desired product. LRMS ([M+H]+)=247.2.

後処理

  1. customwas purged with nitrogen, and 10% Pd/C (200 mg, 20 wt %), ethyl acetate (15 ml), and methanol (5 ml)
  2. additionwere added
  3. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  4. washthe filter cake was washed with methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-cab500ab5a86490caef9a39eb4c7cefb
出典データセット
uspto-grants-2004_03
特許番号
US06706743B2

関連ノート

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