Ammonia → HCID 70626912, compound

HRID 616347Notes

Reaction equation

HRID 616347 reaction equation
[FH:1].[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3].[Br:29]N1C(=O)CCC1=O.N>O.CN(C)C=O>[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@:23]([Br:29])([C@@H:24]([F:1])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 10762617-Hydroxypregna-4,9(11)-diene-3,20-dione 17-acetate

Product 1

HCID 70626912HCID 70626912, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

At -78° C., 20 ml. of hydrogen fluoride is combined with 8 ml. of dimethylformamide, and 6 g. of 17-acetoxy-4,9(11)-pregnadiene-3,20-dione (J. Org. Chem. 26 1961!: 866) and 4 g. of N-bromosuccinimide are added to the reaction mixture. The latter is allowed to stand for 3 hours at -30° C. and then introduced into a mixture of water, ice, and a 25% ammonia solution. The precipitate is filtered off, washed with water, taken up in ethyl acetate, and dried over sodium sulfate. After chromatography of the crude product on silica gel with 19-21.6% acetone/hexane, the yield is 3.0 g. of 17-acetoxy- 9-bromo-11β -fluoro-4-pregnene-3,20-dione; m.p. 180°-182° C. (under decomposition).

Workup

  1. customAt -78° C.
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-62706be1eec24027b8b0a08515d82635
Source dataset
uspto-grants-1978_02
Patent number
US04073900

Reaction notes

Loading…