Hydroxyamine hydrochloride → HCID 131733580, compound

HRID 1749436Notes

Reaction equation

HRID 1749436 reaction equation
[CH3:1][C:2]1([CH3:11])[C:5](=O)[CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].Cl.[NH2:13][OH:14].C(=O)(O)[O-].[Na+]>CO>[OH:14][N:13]=[C:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[C:2]1([CH3:11])[CH3:1]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 12714144Methyl 2,2-diMethyl-3-oxocyclobutanecarboxylate

Product 1

HCID 131733580HCID 131733580, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
11 °C

Procedure

A mixture of methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate (1.0 equiv.), hydroxylamine hydrochloride (1.4 equiv.) and sodium bicarbonate (2.5 equiv.) was suspended in MeOH (0.6 M) and stirred at 11° C. for 12 h. The solvent was removed under reduced pressure, and water was added. The mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was concentrated under reduced pressure to give the crude title product methyl 3-(hydroxyimino)-2,2-dimethyl-cyclobutanecarboxylate (92.7% yield) as a yellow oil, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.73 (s, 3H), 3.27 (dd, J=7.6 Hz, 18.4 Hz, 1H), 3.04 (q, J=9.2 Hz, 18 Hz 1H), 2.89 (t, J=7.2 Hz, 8.8 Hz, 1H), 1.57 (s, 1H), 1.40 (s, 2H), 1.28 (s, 1H), 1.19 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5f1f86bf722412bb3164d29b8293ff3
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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