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

HRID 569321Notes

Reaction equation

HRID 569321 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-118d47d13955474f80255abbc626fdf0
Source dataset
uspto-grants-1988_03
Patent number
US04731367

Reaction notes

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