Hydrochloric Acid → 4-(1-Ethoxy-3-phenyl-2-propyn-1-yl)-N-hydroxybenzenemethanamine
Reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:19])[C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+].[C:26](OCC)(=O)[CH3:27]>C(O)C>[OH:1][NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([O:19][CH2:26][CH3:27])[C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=1Participants
Conditions
- Temperature
- 20 °C
Procedure
To 5 g of 1-(4-hydroxyiminomethylphenyl)-3-phenyl-prop-2-yn-1-ol syn/anti-mixture prepared according to Example 1 and dissolved in 120 ml of ethanol were added 8 ml of borane-pyridine complex at 0° C. and then 12 ml of an ethanolic 20% by weight solution of hydrochloric acid. After stirring at 0° C. for one hour and at 20° C. for 2 hours, the reaction mixture was added to 1.2 liters of a saturated aqueous solution of sodium bicarbonate and shaken with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration and evaporation of the solvent at 40° C. and 2.7×103Pa, the resulting residue (8.1 g) was chromatographed with methylene chloride/methanol 4.7:0.3 to yield 2.3 g of 1-(4-hydroxyaminomethylphenyl)-3-phenyl-1-ethoxy-prop-2-yne in the form of a colorless oil. Following the procedure of Example 1, the resulting oil was converted into N-acetoxy-N-[4-[ 1-ethoxy-3-phenyl-prop-2-yn-1-yl]-benzyl]acetamide and then into the yellow oil of N-hydroxy-N-[4-[1-ethoxy-3-phenyl-prop-2-yn-1-yl]benzyl]acetamide.
Workup
- additionwere added 8 ml of borane-pyridine complex at 0° C.
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationAfter filtration and evaporation of the solvent at 40° C.
- custom2.7×103Pa, the resulting residue (8.1 g) was chromatographed with methylene chloride/methanol 4.7:0.3
Sources & evidence
- ORD record
- ord-5cdbe753a0814735a6fd050c4ca13f59
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05326902
Reaction notes
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