N-bromobutanimide → HCID 12095723, compound

HRID 1986525Notes

Reaction equation

HRID 1986525 reaction equation
[OH:1][C@@:2]1([CH3:29])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C:17]([C@@H:18]([C:20]4[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=4)[CH2:19][C@:3]12[CH3:4])=[C:16]1[C:11](=[CH:12][C:13](=[O:28])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[Br:30]N1C(=O)CCC1=O>O1CCCC1>[Br:30][C:12]1[C:13](=[O:28])[CH2:14][CH2:15][C:16]2[C:11]=1[CH2:10][CH2:9][C@@H:8]1[C:17]=2[C@@H:18]([C:20]2[CH:21]=[CH:22][C:23]([CH:24]=[O:25])=[CH:26][CH:27]=2)[CH2:19][C@@:3]2([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@@:2]2([OH:1])[CH3:29]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12095714HCID 12095714, compound

Product 1

HCID 12095723HCID 12095723, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

781 mg of 4-(17β-hydroxy-17α-methyl-3-oxoestra-4,9-dien-11β-yl)benzaldehyde is dissolved in 25 ml of tetrahydrofuran and mixed with 356 mg of N-bromosuccinimide. The mixture is stirred for 2 hours at room temperature, then poured into 200 ml of ice water. The precipitate is filtered off, washed neutral and dried. After purification by means of preparative layer chromatography, 475 mg of 4-(4′-bromo-17β-hydroxy-17α-methyl-3-oxoestra-4,9-dien-11β-yl)benzaldehyde is obtained as a foam, which is incorporated directly into the oximization analogously to Example 1 with hydroxylammonium hydrochloride in pyridine.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed neutral
  3. customdried
  4. customAfter purification by means of preparative layer chromatography

Sources & evidence

ORD record
ord-7e0fadbc980a4a1c9b2ea35cb0676e15
Source dataset
uspto-grants-2009_06
Patent number
US07550451B2

Reaction notes

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