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Water → 1,1-Diethyl-3-(2,6-dimethyl-13-hydroxymethyl-8alpha-ergolinyl)-urea

HRID 35852
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HRID 35852 반응식
[CH2:1]([N:3]([CH2:27][CH3:28])[C:4](=[O:26])[NH:5][C@H:6]1[CH2:20][C@H:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][C:16]([CH:22]=[O:23])=[CH:17][C:18]2=4)[NH:13][C:12]=3[CH3:24])[N:8]([CH3:25])[CH2:7]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:27]([N:3]([CH2:1][CH3:2])[C:4]([NH:5][C@H:6]1[CH2:20][C@H:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][C:16]([CH2:22][OH:23])=[CH:17][C:18]2=4)[NH:13][C:12]=3[CH3:24])[N:8]([CH3:25])[CH2:7]1)=[O:26])[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 88424208HCID 88424208, 화합물

생성물 1

HCID 677875701,1-Diethyl-3-(2,6-dimethyl-13-hydroxymethyl-8alpha-ergolinyl)-urea

시약·촉매·용매 2

HCID 6212
Chloroform
용매
HCID 8028Tetrahydrofuran용매

실험 절차

370 mg of 8alpha-(3,3-diethylureido)-2,6-dimethyl-ergoline-13-carbaldehyde (1 mmol) is dissolved in 50 ml of tetrahydrofuran and reduced with 200 mg of lithium aluminum hydride at room temperature for 1 hour. The mixture is cooled off in an ice bath and mixed in succession with 0.2 ml of water, 0.2 ml of 15% sodium hydroxide solution and 0.6 ml of water, the precipitate is filtered off and the filtrate is evaporated to dryness. The residue is chromatographed on silica gel with dichloromethane/methanol. 243 mg of alcohol, which crystallizes from ethyl acetate, is isolated. Yield 166 mg (44% of theory), [α]D =+6° (0.5% in chloroform).

후처리

  1. temperatureThe mixture is cooled off in an ice bath
  2. filtrationthe precipitate is filtered off
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is chromatographed on silica gel with dichloromethane/methanol
  5. custom243 mg of alcohol, which crystallizes from ethyl acetate
  6. customis isolated

출처 및 근거

ORD 기록
ord-d6a9c26a5d3d4b0980ec7483817a2fca
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05411966

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