O-Methylhydroxylamine hydrochloride → HCID 72998856, compound

HRID 2103030Notes

Reaction equation

HRID 2103030 reaction equation
OC[CH:3]1[C:12]2([CH2:15][CH2:14][CH2:13]2)[O:11][C:10]2[C:5](=[C:6]([CH3:19])[C:7]([OH:18])=[C:8]([CH3:17])[C:9]=2[CH3:16])[CH2:4]1.Cl.[CH3:21][O:22][NH2:23]>N1C=CC=CC=1>[CH3:21][O:22][N:23]=[CH:4][C:3]1[C:12]2([CH2:13][CH2:14][CH2:15]2)[O:11][C:10]2[C:9](=[C:8]([CH3:17])[C:7]([OH:18])=[C:6]([CH3:19])[CH:5]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69053370HCID 69053370, compound

Product 1

HCID 72998856HCID 72998856, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde (421 mg, prepared as described in Example 19) in 8 mL of pyridine was added methoxyamine hydrochloride (628 mg). The reaction mixture was allowed to stir at room temperature overnight. The mixture was extracted with ethyl acetate and washed with 1N HCl. The organic solvent was evaporated in vacuo, the residue was purified by flash chromatography eluted with 10% ethyl acetate in hexane to give 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde O-methyloxime as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=7.82 (s, 1H), 6.68 (s, 1H), 6.60 (s, 1H), 4.45 (s, 1H), 3.98 (s, 3H), 2.75 (m, 2H), 2.44 (m, 2H), 2.40 (s, 3H), 2.22 (s, 3H), 1.98 (m, 2H) ppm. 13C-NMR (75 MHz, CDCl3) δ=148.6, 146.5, 146.4, 131.2, 125.8, 125.1, 119.9, 119.6, 116.0, 80.5, 62.1, 34.2, 16.6, 13.6, 11.4 ppm. MS: (m/z)=274.0 (M+H+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with 1N HCl
  3. customThe organic solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f4dd180cbe69424591aa7c721491bf6f
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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