N-bromobutanimide → HCID 70406261, compound

HRID 414205Notes

Reaction equation

HRID 414205 reaction equation
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:3]1.[Br:25]N1C(=O)CCC1=O>O1CCOCC1>[Br:25][C:13]1[NH:12][C:11]2[C:17]3[C:14]=1[CH2:15][C@@H:16]1[C:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:5][C@H:4]([NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:3][N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70406371HCID 70406371, compound

Product 1

HCID 70406261HCID 70406261, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.5 g 6-methyl-8α-pivaloylamino-9,10-didehydro-ergoline in 120 ml dioxane is treated with 960 mg N-bromosuccinimide and the resulting mixture stirred at room temperature overnight The reaction mixture is then evaporated and the residue partitioned between ethyl acetate and 2N Na2CO3. The organic layers are dried (Na2SO4), evaporated and chromatographed on 80 g silica gel using 98:2 CH2Cl2 /CH3OH. Crystallization from ether gives the title compound, m.p. 169°-171°.

Workup

  1. customis then evaporated
  2. customthe residue partitioned between ethyl acetate and 2N Na2CO3
  3. dry with materialThe organic layers are dried (Na2SO4)
  4. customevaporated
  5. customchromatographed on 80 g silica gel using 98:2 CH2Cl2 /CH3OH
  6. customCrystallization from ether

Sources & evidence

ORD record
ord-5f5332339bcd423db4910cb1f8761575
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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