Hydrofluoric Acid → HCID 70635233, compound

HRID 596980Notes

Reaction equation

HRID 596980 reaction equation
[FH:1].[Br:2]N1C(=O)CCC1=O.[OH:10][C@H:11]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:17]3[C@H:18]3[CH2:37][C@H:19]3[C@@H:20]2[C:21](=[O:27])[CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH2:12]1.C(=O)(O)[O-].[K+]>C(Cl)Cl.CN(C)C=O>[F:1][C@H:14]1[C@:13]2([Br:2])[C@:32]([CH3:35])([CH2:33][CH2:34][C@H:11]([OH:10])[CH2:12]2)[C@@H:31]2[C@H:16]([C@H:17]3[C@:28]([CH3:36])([CH2:29][CH2:30]2)[C@@H:20]([C:21](=[O:27])[CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:19]2[CH2:37][C@H:18]32)[CH2:15]1

Participants

7

Reactant 4

HCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 516893Potassium BicarbonateHCID 70634210HCID 70634210, compound

Product 1

HCID 70635233HCID 70635233, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

2.5 ml of liquid hydrogen fluoride is added to 2.5 ml. of dimethylformamide cooled to -40° C. The reaction mixture is combined with 250 mg. of N-bromosuccinimide, and then 500 mg. of 3β-hydroxy-21-acetoxy-15α,16α-methylene-5-pregnen-20-one, dissolved in 5 ml. of methylene chloride, is introduced into this reaction mixture. The latter is agitated for 5 minutes at -15° C., poured into saturated potassium bicarbonate solution, and extracted with methylene chloride. After drying and evaporation, 700 mg. of crude 6β-fluoro-5-bromo-3β-hydroxy-21-acetoxy-15α,16α-methylene-5α-pregnan-20-one is obtained.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter drying
  3. customevaporation, 700 mg

Sources & evidence

ORD record
ord-0d337fc45ffe4f7aa9eb54d9cc934138
Source dataset
uspto-grants-1977_03
Patent number
US04012510

Reaction notes

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