8alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester → 8alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acid

HRID 231702Notes

Reaction equation

HRID 231702 reaction equation
C([O:8][C:9]([C:11]1[NH:25][C:24]2[C:26]3[C:12]=1[CH2:13][C@@H:14]1[C@@H:19]([C:20]=3[CH:21]=[CH:22][CH:23]=2)[CH2:18][C@H:17]([NH:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])[CH2:16][N:15]1[CH3:35])=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH2:33]([N:30]([CH2:31][CH3:32])[C:28](=[O:29])[NH:27][C@H:17]1[CH2:18][C@H:19]2[C@@H:14]([CH2:13][C:12]3[C:26]4[C:24](=[CH:23][CH:22]=[CH:21][C:20]2=4)[NH:25][C:11]=3[C:9]([OH:10])=[O:8])[N:15]([CH3:35])[CH2:16]1)[CH3:34]

Participants

4

Reactant 1

HCID 135590328alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester

Product 1

HCID 135590348alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

104 mg (0.22 mmol) of 8α-(3,3-diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester is dissolved in 20 ml of methanol and, after adding 50 mg of palladium black, hydrogenated for 30 minutes under normal pressure at room temperature. After the catalyst has been filtered off and the mixture concentrated, 8α-(3,3-diethylureido)-6-methylergoline-2-carboxylic acid is obtained in a 100% yield, mp: decomposition starting with 230° C.

Workup

  1. filtrationAfter the catalyst has been filtered off
  2. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-8673d8affaa5406d84ad1d7b1364609b
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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