HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 35852
Notes
Print preview

Reaction equation

HRID 35852 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 88424208HCID 88424208, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d6a9c26a5d3d4b0980ec7483817a2fca
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05411966

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes