O-Methylhydroxylamine hydrochloride → HCID 178502616, compound

HRID 1182867Notes

Reaction equation

HRID 1182867 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH:9]1[CH2:13][CH2:12][C@@H:11]([O:14]/[N:15]=[C:16]2\[CH2:17][CH:18]3[C@:31]([CH3:35])([CH2:32][C@H:33]\2[F:34])[C@@H:30]2[C@H:21]([C@H:22]4[C@@:26]([CH2:28][CH2:29]2)([CH3:27])[C@@H:25]([OH:36])[CH2:24][CH2:23]4)[CH2:20][C:19]3=O)[CH2:10]1.Cl.[CH3:39][O:40][NH2:41]>>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH:9]1[CH2:13][CH2:12][C@@H:11]([O:14]/[N:15]=[C:16]2\[CH2:17][CH:18]3[C@:31]([CH3:35])([CH2:32][C@H:33]\2[F:34])[C@@H:30]2[C@H:21]([C@H:22]4[C@@:26]([CH2:28][CH2:29]2)([CH3:27])[C@@H:25]([OH:36])[CH2:24][CH2:23]4)[CH2:20]/[C:19]/3=[N:41]\[O:40][CH3:39])[CH2:10]1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 87552262HCID 87552262, compound

Product 1

HCID 178502616HCID 178502616, compound

Procedure

The title compound was obtained in 56% yield following the procedure described in Example 34 starting from (E)-3-[3-(R)-pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate (Example 35, 72 mg) and methoxyamine hydrochloride (14 mg). After evaporation of the solvent the crude reaction mixture was purified by flash chromatography (SiO2, CHCl3/MeOH/26% NH4OH 90/10/1). To the concentrated fractions, a stoichiometric amount of fumaric acid in MeOH was added. The resulting precipitate was rinsed with heptane and filtered to give the title compound I-bk.

Workup

  1. customAfter evaporation of the solvent the crude
  2. customreaction mixture
  3. customwas purified by flash chromatography (SiO2, CHCl3/MeOH/26% NH4OH 90/10/1)
  4. additionTo the concentrated fractions, a stoichiometric amount of fumaric acid in MeOH was added
  5. washThe resulting precipitate was rinsed with heptane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-583f53294cd44b129c8a7642c0e7f8b1
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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