Bromine → HCID 86734034, compound

HRID 1576798Notes

Reaction equation

HRID 1576798 reaction equation
[Br:1][C@H:2]1[C@H:21]([OH:22])[CH2:20][CH2:19][C@@:18]2([CH3:23])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:17]2[C:16](=[O:24])[CH2:15][C@@:14]2([CH3:25])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C:11](=[O:13])[CH3:12].[Br:26]Br>CO.O>[Br:1][C@H:2]1[C@H:21]([OH:22])[CH2:20][CH2:19][C@@:18]2([CH3:23])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:17]2[C:16](=[O:24])[CH2:15][C@@:14]2([CH3:25])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C:11](=[O:13])[CH2:12][Br:26]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 131710461HCID 131710461, compound

Product 1

HCID 86734034HCID 86734034, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

4β-Bromo-3α-hydroxy-5α-pregnane-11,20-dione (945 mg) in dry methanol (70 ml.) at 10° was treated with a solution of bromine (0.125 ml.) in methanol (5 ml.) dropwise over 7 hours, at such a rate that the bromine colour was taken up during the addition. The reaction solution was then stirred at room temperature for 30 minutes until it became colourless, and it was then diluted with water (300 ml.) and the white precipitate was extracted into methylene chloride. The organic solution was washed with water, dried over sodium sulphate and evaporated to a white foam (1.2 g.) which was purified by preparative T.L.C. in ethyl acetate/benzene 1/3 the upper (major) band giving 660 mg. of a white solid which was triturated with ether to give title compound (580 mg.) as white crystals, m.p. 164°-166°, [α]D + 76° (c 1.35).

Workup

  1. extractionthe white precipitate was extracted into methylene chloride
  2. washThe organic solution was washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to a white foam (1.2 g.) which
  5. customwas purified by preparative T.L.C
  6. customin ethyl acetate/benzene 1/3 the upper (major) band giving 660 mg
  7. customof a white solid which was triturated with ether

Sources & evidence

ORD record
ord-804f89bfc2a44331ba0362b57a57a9bb
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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