2,4,6-Trimethylpyridine → HCID 70634572, compound

HRID 436363Notes

Reaction equation

HRID 436363 reaction equation
[F:1][C@@H:2]1[C:29]2[C@:24]([CH3:31])([CH:25]=[CH:26][C:27](=[O:30])[CH:28]=2)[C@:23]2(Br)[C@H:4]([C@H:5]3[C@:20]([CH3:34])([CH2:21][C@@H:22]2[OH:33])[C@@H:8]([C:9](=[O:19])[CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C@H:7]([CH3:35])[CH2:6]3)[CH2:3]1.N1C(C)=CC(C)=CC=1C>>[F:1][C@@H:2]1[C:29]2[C@:24]([CH3:31])([CH:25]=[CH:26][C:27](=[O:30])[CH:28]=2)[C:23]2[C@@H:22]([OH:33])[CH2:21][C@@:20]3([CH3:34])[C@@H:5]([CH2:6][C@@H:7]([CH3:35])[C@@H:8]3[C:9](=[O:19])[CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 79532,4,6-TrimethylpyridineHCID 70634018HCID 70634018, compound

Product 1

HCID 70634572HCID 70634572, compound

Procedure

15.0 g. of 6α-fluoro-9α-bromo-11β-hydroxy-21-hexanoyloxy-16α-methyl-1,4-pregnadiene-3,20-dione is dissolved in 25 ml. of collidine and agitated for 15 minutes at 170° C. After cooling, the collidine hydrobromide is filtered off and the filtrate combined with ether until no precipitate is formed any longer. The precipitate is filtered off, and the filtrate is extracted with hydrochloric acid and sodium bicarbonate; then, it is washed neutral, dried, and concentrated. The viscous crude product amounting to 17.7 g. is purified by chromatography over a silica gel column, and recrystallization from acetone-hexane yields 6α-fluoro-11β-hydroxy-21-hexanoyloxy-16α-methyl-1,4,8-pregnatriene-3,20-dione, m.p. 155° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe collidine hydrobromide is filtered off
  3. customis formed any longer
  4. filtrationThe precipitate is filtered off
  5. extractionthe filtrate is extracted with hydrochloric acid and sodium bicarbonate
  6. washthen, it is washed neutral
  7. customdried
  8. concentrationconcentrated
  9. customis purified by chromatography over a silica gel column, and recrystallization from acetone-hexane

Sources & evidence

ORD record
ord-8136cc60917043a88ed456b1e9ebb8d1
Source dataset
uspto-grants-1977_02
Patent number
US04008313

Reaction notes

Loading…