Trifluoroacetic acid → HCID 57200943, compound

HRID 1730275Notes

Reaction equation

HRID 1730275 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H: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)[CH2:5][CH:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]1.FC(F)(F)C(O)=O.[BH4-].[Na+].[OH-].[NH4+]>>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[CH:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][CH:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 12727276Methyl 6-methylergoline-8-carboxylate

Product 1

HCID 57200943HCID 57200943, compound

Procedure

A solution of 0.7 g. of 6-methyl-8-carbomethoxyergoline in 50 ml. of trifluoroacetic acid was stirred and cooled to 5° c. in an ice-water bath. To the cold reaction mixture was added 1 g. of sodium borohydride in equal portions over about 1/2 hour. The reaction mixture was added 50 g. of ice and ammonium hydroxide was added to adjust the pH to 11. The aqueous alkaline reaction mixture was extracted with ethyl acetate, and the combined organic extracts were washed with water, dried, and the solvent was removed therefrom providing 2,3-dihydro-6-methyl-8-carbomethoxy-ergoline as an oil. The oil was added to a column containing 30 g. of florisil, and the column was eluted with chloroform containing 1 percent methanol. Fractions of 50 ml. each were collected, and fractions 25-35 were combined, the solvent was removed therefrom under reduced pressure to afford an oil which was crystallized from diethyl ether and hexane and shown to be 2,3-dihydro-6-methyl-8carbomethoxy-ergoline, M.P. 110°-120° C.

Workup

  1. temperaturecooled to 5° c
  2. customTo the cold reaction mixture
  3. additionwas added 1 g
  4. additionThe reaction mixture was added 50 g
  5. customThe aqueous alkaline reaction mixture
  6. extractionwas extracted with ethyl acetate
  7. washthe combined organic extracts were washed with water
  8. customdried
  9. customthe solvent was removed
  10. additionThe oil was added to a column
  11. additioncontaining 30 g
  12. washof florisil, and the column was eluted with chloroform containing 1 percent methanol
  13. customeach were collected
  14. customthe solvent was removed
  15. customunder reduced pressure to afford an oil which
  16. customwas crystallized from diethyl ether and hexane

Sources & evidence

ORD record
ord-194ab94fcdfd4fdfbe8e12e99260d47d
Source dataset
uspto-grants-1976_11
Patent number
US03992385

Reaction notes

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