O-Methylhydroxylamine hydrochloride → HCID 73047665, compound

HRID 2102997Notes

Reaction equation

HRID 2102997 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[S:8][C:7]1([CH2:16][CH2:15][CH2:14]1)[CH2:6][C:5]2=O.Cl.[CH3:20][O:21][NH2:22]>N1C=CC=CC=1>[CH3:20][O:21][N:22]=[C:5]1[C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=2[CH3:18])[S:8][C:7]2([CH2:16][CH2:15][CH2:14]2)[CH2:6]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 11673358HCID 11673358, compound

Product 1

HCID 73047665HCID 73047665, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6′-hydroxy-5′,7′,8′-trimethylspiro[cyclobutane-1,2′-thiochromen]-4′(3′H)-one prepared as described above (300 mg) in 2 mL of pyridine was added methoxyamine hydrochloride (192 mg, 2.3 mmol). The reaction mixture was allowed to stir overnight. The mixture was washed with water and extracted with ethyl acetate. After concentration in vacuo, the residue was purified by flash chromatography eluted with 20% ethyl acetate in hexane to give 150 mg of 6′-hydroxy-5′,7′,8′-trimethylspiro[cyclobutane-1,2′-thiochromen]-4′(3′H)-one O-methyloxime, as a white solid.

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-10af068388734dd0b864fe4503903f56
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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