Bicyclo(2.2.1)heptan-2-one → 1-Methyl-5-[3-(Bicyclo[2.2.1]hept-2-ylamino)-4-Methoxyphenyl]-2-Imidazolidinone

HRID 2210486

反応式

HRID 2210486 の反応式
[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([NH2:15])[CH:8]=2)[CH2:5][NH:4][C:3]1=[O:16].[CH2:17]1[CH:21]2[CH2:22][C:23](=O)[CH:19]([CH2:20]2)[CH2:18]1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.CCOCC.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([NH:15][CH:18]3[CH2:17][CH:21]4[CH2:20][CH:19]3[CH2:23][CH2:22]4)[CH:8]=2)[CH2:5][NH:4][C:3]1=[O:16]

参加物

8

反応物 4

HCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 193788821-Methyl-5-(3-Amino-4-Methoxyphenyl)-2-Imidazolidinone

生成物 1

HCID 140102051-Methyl-5-[3-(Bicyclo[2.2.1]hept-2-ylamino)-4-Methoxyphenyl]-2-Imidazolidinone収率 10.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

The aniline of Example 51 (3.07 g, 17.95 mmol) is dissolved in 60 ml of glacial acetic acid and to this is added norcamphor (2.37 g, 21.54 mmol). The reaction is cooled to 5° C. and to it is added sodium cyanoborohydride (1.36 g, 21.54 mmol). The reaction is poured onto ice and is pH adjusted to 7 with 1 normal NaOH solution. The aqueous is extracted with methylene chloride dried over MgSO4, filtered and concentrated in vacuo to afford a brown oil which is flashed on SiO2 with ethyl acetate as the eluent. The appropriate fractions are combined and concentrated in vacuo to yield a white paste which is tritarted with ether to yield 0.57 g (10%) of the product as a white crystalline solid. MP=171°-174° C.

後処理

  1. additionThe reaction is poured onto ice
  2. extractionThe aqueous is extracted with methylene chloride
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a brown oil which
  7. concentrationconcentrated in vacuo
  8. customto yield a white paste which

出典と根拠

ORDレコード
ord-696f52dc4c5242149f4136b0d12c4761
出典データセット
uspto-grants-1995_10
特許番号
US05459145

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