Water → HCID 10539784, compound

HRID 47055Notes

Reaction equation

HRID 47055 reaction equation
[CH3:1][N:2]1[C:16]2[C:17]3[C:4]([CH2:5][C@@H:6]4[C:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)=[CH:10][C@@H:9]([CH2:18][N:19]=[N+]=[N-])[CH2:8][N:7]4[CH3:22])=[CH:3]1.[BH4-].[Na+].O>C(O)(C)C>[CH3:1][N:2]1[C:16]2[C:17]3[C:4]([CH2:5][C@@H:6]4[C:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)=[CH:10][C@@H:9]([CH2:18][NH2:19])[CH2:8][N:7]4[CH3:22])=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 867367091,6-Dimethyl-8beta-azidomethyl-9, 10-didehydroergoline

Product 1

HCID 10539784HCID 10539784, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.2 g 1,6-dimethyl-8β-azidomethyl-9, 10-didehydroergoline in 150 mls of isopropyl alcohol are treated with 6.4 g NaBH4 and heated to reflux under stirring and under nitrogen atmosphere for 24 hours. After this time further 2 g of NaBH4 are added and the heating is continued for 24 hours more. The reaction mixture is poured into water and extracted with chloroform. The chloroform extract is chromatographed onto SiO2 and the product is eluted with CH2Cl2 /MeOH/NH4OH (9/1/0.5). 1.6 g of 1,6-dimethyl-8β-aminomethyl-9, 10-didehydroergoline are thus obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. waitthe heating is continued for 24 hours
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customis chromatographed onto SiO2
  7. washthe product is eluted with CH2Cl2 /MeOH/NH4OH (9/1/0.5)

Sources & evidence

ORD record
ord-643e6bd49d9e4e7c9555a88a8804197e
Source dataset
uspto-grants-1979_11
Patent number
US04176182

Reaction notes

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