Ammonia → HCID 68146927, compound

HRID 1658702Notes

Reaction equation

HRID 1658702 reaction equation
[FH:1].[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C:22](=[CH:23][CH2:24][C@:7]12[CH3:8])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:4])[CH3:3].[Br:26]N1C(=O)CCC1=O.N>CN(C)C=O>[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@:22]([Br:26])([C@@H:23]([F:1])[CH2:24][C@:7]12[CH3:8])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 22791149HCID 22791149, compound

Product 1

HCID 68146927HCID 68146927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At -78°, 80 ml. of hydrogen fluoride is combined with 32 ml. of dimethylformamide, 22 g. of 17β-acetoxy-4,9(11)-androstadien-3-one, and 16 g. of N-bromosuccinimide. The mixture is allowed to stand for 1.5 hours at -30° and then introduced into a mixture of ice/water and a 25% ammonia solution. The precipitate is filtered off, dissolved in a mixture of ethyl acetate and methylene chloride, washed with water, and dried over sodium sulfate. After chromatography with acetone/hexane, 9.1 g of 17β-acetoxy-9-bromo-11β-fluoro-4-androsten-3-one is obtained; m.p. 172°-174° UV: ε239 = 16,300 (methanol).

Workup

  1. customAt -78°
  2. filtrationThe precipitate is filtered off
  3. dissolutiondissolved in a mixture of ethyl acetate and methylene chloride
  4. washwashed with water
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-2ce3e51824aa450eba2ebda328ce590e
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

Loading…