Hydroxylamine → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxyfuran-3-carboximidamide
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[O:14][CH:13]=[C:12]([C:15]#[N:16])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:17][OH:18].O>C(O)C.CCOCC>[Si:1]([O:8][CH2:9][C:10]1[O:14][CH:13]=[C:12]([C:15](=[N:17][OH:18])[NH2:16])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-furonitrile (1.8 g, 7.6 mmol) that was obtained in Example 1 (1c) in ethanol (10 ml) was added a 40% aqueous solution of hydroxylamine (1.0 ml) with stirring, and the resulting mixture was stirred at 60° C. for 1 hour. After evaporating the reaction mixture in vacuo, the residue obtained was diluted with ether, poured into water (40 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (2.0 g) in a yield of 97% as a white crystalline solid.
Workup
- stirringthe resulting mixture was stirred at 60° C. for 1 hour
- customAfter evaporating the reaction mixture in vacuo
- customthe residue obtained
- extractionextracted with ether
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration
- customthe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-be3e4a1c91a14d39b2449544ee5a8503
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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