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

HRID 2210486

반응식

HRID 2210486 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-696f52dc4c5242149f4136b0d12c4761
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05459145

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