Hydroxyamine hydrochloride → 3-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

HRID 440085

Reaction equation

HRID 440085 reaction equation
Cl.NO.C1([NH:10][C:11]([CH3:21])=[CH:12][C:13]([CH:15]2[N:19]([CH3:20])[CH2:18][CH2:17][CH2:16]2)=[O:14])CCCCC1>CO>[CH3:21][C:11]1[CH:12]=[C:13]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:19]2[CH3:20])[O:14][N:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 677344693-(Cyclohexylamino)-1-(1-methyl-5-pyrrolidinyl)-2-butene-1-one

Product 1

HCID 1193803-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Hydroxylamine HCl (70 mg, 1.0 mmol) was added to a solution of 3-(cyclohexylamino)-1-(1-methyl-5-pyrrolidinyl)-2-butene-1-one (160 mg, 0.64 mmol, from step 12a above) in 5 mL of methanol, and the mixture was stirred at 20±5° C. for 4 hr. The solvent was removed under vacuum at 25° C., and the residue suspended in 3 mL of water and 1 mL of H2SO4. The mixture was heated to 70° C. for 90 min, then cooled to room temperature and adjusted to pH 10 with 50% NaOH (4 g). The mixture was extracted with ethyl acetate, and the extracts were dried over Na2SO4 and concentrated. The residue was confirmed as title product by chromatographic analysis. The analytical data correspond to that given in Example 1.

Workup

  1. customThe solvent was removed under vacuum at 25° C.
  2. temperatureThe mixture was heated to 70° C. for 90 min
  3. temperaturecooled to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extracts were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3d197f8ad3447fb31c47426e6db5d7
Source dataset
uspto-grants-1996_05
Patent number
US05516912

Linked notes

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