Hydroxyamine hydrochloride → 3-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °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
- customThe solvent was removed under vacuum at 25° C.
- temperaturecooled to room temperature
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe extracts were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5be8ad001edd4123a55be42a7b40d433
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05559242
Reaction notes
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