Hydrochloric Acid → 4-Chloro-16alpha-fluoro-1,6beta-dimethyl-7-methylen-androsta-1,4-diene-3,17-dione

HRID 621628Notes

Reaction equation

HRID 621628 reaction equation
O1[C:3]23[C@:16]([CH3:22])([C:17]([CH3:21])=[CH:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:23])[C@H:9]([F:24])[CH2:8]2)[C:5](=[CH2:25])[C@H:4]3[CH3:26].[ClH:27]>C(O)(=O)C>[Cl:27][C:2]1[C:19](=[O:20])[CH:18]=[C:17]([CH3:21])[C@@:16]2([CH3:22])[C:3]=1[C@H:4]([CH3:26])[C:5](=[CH2:25])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][C@@H:9]([F:24])[C:10]2=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18632049HCID 18632049, compound

Product 1

HCID 186320514-Chloro-16alpha-fluoro-1,6beta-dimethyl-7-methylen-androsta-1,4-diene-3,17-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4,5-epoxy-16α-fluoro-1,6β-dimethyl-7-methylenandrost-1-ene-3,17-dione (359 mg) in glacial acetic acid (5 ml) is treated with gaseous hydrogen chloride for about 30 min at room temperature. The precipitate is filtered off, washed with diethylether and then chromatographed on silica gel to give pure 4-chloro-16α-fluoro-1,6β-dimethyl-7-methylen-androsta-1,4-diene-3,17-dione (245 mg).

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with diethylether
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-085f1d960c17479095f2aabda0bef861
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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