Water → 8alpha-Benzyloxycarbonylaminoergoline

HRID 34955Notes

Reaction equation

HRID 34955 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)[N:14](C#N)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(O)(=O)C.[Zn]>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 867423318alpha-Benzyloxycarbonylamino-6-cyanoergoline

Product 1

HCID 704180878alpha-Benzyloxycarbonylaminoergoline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

18 g (46.5 mM) of 8α-benzyloxycarbonylamino-6-cyanoergoline obtained from step (b) in 100 ml acetic acid are added to a suspension of 40 g zinc in 100 ml acetic acid. 40 ml water are added and the mixture is heated at 100° for 10 hours. To work up, the mixture is filtered through a filtering aid such as Hyflo and concentrated in a rotary evaporator. The residue is partitioned between potassium bicarbonate aqueous solution and methylene chloride/isopropanol (b 9:1). The organic phase is dried over sodium sulphate, filtered and concentrated to give the heading compound in crude form.

Workup

  1. temperaturethe mixture is heated at 100° for 10 hours
  2. filtrationthe mixture is filtered through a filtering aid such as Hyflo
  3. concentrationconcentrated in a rotary evaporator
  4. customThe residue is partitioned between potassium bicarbonate aqueous solution and methylene chloride/isopropanol (b 9:1)
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the heading compound in crude form

Sources & evidence

ORD record
ord-d93aa06583224a479e269facca911fe3
Source dataset
uspto-grants-1988_08
Patent number
US04764517

Reaction notes

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