Ammonia → HCID 67788131, compound

HRID 35857Notes

Reaction equation

HRID 35857 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[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]([C:23](O)([CH3:25])[CH3:24])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:27])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:2].[BH4-].[Na+].N>C(O)(=O)C>[CH2:29]([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]([CH:23]([CH3:24])[CH3:25])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:27])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:30]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 67788699HCID 67788699, compound

Product 1

HCID 67788131HCID 67788131, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,1-Diethyl-3-[13-(1-hydroxy-1-methyl-1-ethyl)-2,6-dimethyl- 8alpha-ergolinyl]-urea (0.5 mmol) is dissolved in 5 ml of glacial acetic acid and 0.25 g of sodium borohydride is added. After 15 minutes of stirring at room temperature, ice is added, it is made alkaline with conc. ammonia and extracted with ethyl acetate. The organic phases are dried with sodium sulfate and concentrated by evaporation, the residue is chromatographed on silica gel with dichloromethane/methanol, yield 76 mg (38% of theory).

Workup

  1. additionice is added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phases are dried with sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is chromatographed on silica gel with dichloromethane/methanol, yield 76 mg (38% of theory)

Sources & evidence

ORD record
ord-31e0ef1f372143e2a2c7ecdeaa882543
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Reaction notes

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