Trifluoroacetic acid → HCID 70397966, compound

HRID 1730274Notes

Reaction equation

HRID 1730274 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]([CH2:18][C:19]#[N:20])[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]([CH2:18][C:19]#[N:20])[CH2:3]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 12782967HCID 12782967, compound

Product 1

HCID 70397966HCID 70397966, compound

Procedure

A solution of 4.1 g. of 6-methyl-8-cyanomethyl-ergoline in 110 ml. of trifluoroacetic acid was stirred and cooled to 5° C. in a ice-waterbath. To the cold solution was added 2.5 g. of sodium borohydride, in 5 equal portions over 1 hour. The reaction mixture was added to 100 g. of ice and the pH of the aqueous reaction mixture was adjusted to 11 by the addition of ammonium hydroxide. The aqueous alkaline reaction mixture was extracted with chloroform. The combined organic extracts were washed with water, dried, and the solvent was evaporated therefrom to provide 2,3-dihydro-6-methyl-8-cyanomethylergoline, M.P. 100°-104° C.

Workup

  1. additionTo the cold solution was added 2.5 g
  2. additionThe reaction mixture was added to 100 g
  3. customThe aqueous alkaline reaction mixture
  4. extractionwas extracted with chloroform
  5. washThe combined organic extracts were washed with water
  6. customdried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-810ee387b25143009c29387516816051
Source dataset
uspto-grants-1976_11
Patent number
US03992385

Reaction notes

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