Allyl acetate → Cabergoline

HRID 2267082Notes

Reaction equation

HRID 2267082 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][CH2:5][N:6]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[NH:11][CH2:10]1)=[O:8].C(O[CH2:35][CH:36]=[CH2:37])(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:37]([N:11]1[C@H:12]2[C@@H:22]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]4[C:24]=3[C:14]([CH2:13]2)=[CH:15][NH:16]4)[CH2:23][C@@H:9]([C:7]([N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:30])[C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[O:8])[CH2:10]1)[CH:36]=[CH2:35]

Participants

5

Reactant 2

HCID 11584Allyl acetateHCID 9979008Des-N-allylcabergoline

Product 1

HCID 54746CabergolineYield 92.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a suspension of 9.0 g (21.87 mmol) N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl)-ergoline-8β-carboxamide (XIX) in 250 ml of toluene 0.5 g of tetrakis(triphenylphosphine)palladium(0) and 5 ml of allyl acetate was added, and the reaction mixture was stirred at ambient temperature for 2 hours. The resulting mixture was washed with 100 ml of water. The organic layer was dried over anhydrous sodium sulphate. The dried solution was concentrated in vacuum and the product was purified on a silica plug to give 9.1 g (92.3%) of the title compound.

Workup

  1. additionwas added
  2. washThe resulting mixture was washed with 100 ml of water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationThe dried solution was concentrated in vacuum
  5. customthe product was purified on a silica plug

Sources & evidence

ORD record
ord-c817a92571974bdc94728898e3237df6
Source dataset
uspto-grants-2010_12
Patent number
US07858791B2

Reaction notes

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