1,1-Diethyl-3-[13-(1,3-dithiolan-2-yl)-2,6-dimethyl-8alphaergolinyl]-urea → HCID 67788086, compound

HRID 35853

Reaction equation

HRID 35853 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][C:17]([CH:23]5SCCS5)=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:28])[N:9]([CH3:29])[CH2:8]1)=[O:5])[CH3:2]>CO.[Ni]>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][C:17]([CH3:23])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:28])[N:9]([CH3:29])[CH2:8]1)=[O:5])[CH3:31]

Participants

4

Reactant 1

HCID 867486521,1-Diethyl-3-[13-(1,3-dithiolan-2-yl)-2,6-dimethyl-8alphaergolinyl]-urea

Product 1

HCID 67788086HCID 67788086, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

458 mg of 1,1-diethyl-3-[13-(1,3-dithiolan-2-yl)-2,6- dimethyl-8alpha-ergolinyl)-urea (1 mmol) is dissolved in 50 ml of methanol and treated with several portions of Raney nickel at room temperature until the initial material has disappeared according to thin-layer chromatography. It is filtered by kieselguhr, the solvent is concentrated by evaporation and the residue is chromatographed on silica gel with dichloromethane/methanol, the isolated substance is crystallized from methanol, yield 117 mg (31% of theory).

Workup

  1. filtrationIt is filtered by kieselguhr
  2. concentrationthe solvent is concentrated by evaporation
  3. customthe residue is chromatographed on silica gel with dichloromethane/methanol
  4. customthe isolated substance is crystallized from methanol, yield 117 mg (31% of theory)

Sources & evidence

ORD record
ord-3a04d62722a1452cb1bc6d1b5841f32e
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Linked notes

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