Potassium Carbonate → 8alpha-Benzyloxycarbonylamino-6-n-propylergoline

HRID 34956Notes

Reaction equation

HRID 34956 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:26][C@H:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[NH:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](I)[CH2:35][CH3:36]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:26][C@H:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:14]([CH2:34][CH2:35][CH3:36])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 704180878alpha-Benzyloxycarbonylaminoergoline

Product 1

HCID 139664588alpha-Benzyloxycarbonylamino-6-n-propylergoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 17.5 g (ca. 46 mM) of 8α-benzyloxycarbonylaminoergoline obtained from step (c), 13.5 g potassium carbonate and 6 ml (62 mM) n-propyl iodide in 300 ml dimethylformamide is stirred for 18 hours at room temperature. The mixture is filtered and concentrated in a rotary evaporator. The residue is treated with methylene chloride and shaken with water. The organic phase is dried over sodium sulphate, filtered and concentrated to give the crude heading compound.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in a rotary evaporator
  3. additionThe residue is treated with methylene chloride
  4. stirringshaken with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude

Sources & evidence

ORD record
ord-89af1d7fd8184661a3b3f11df6dec6aa
Source dataset
uspto-grants-1988_08
Patent number
US04764517

Reaction notes

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