N-cyclopentylhydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in Example 42 using 2-ethoxybenzaldehyde and N-cyclopentylhydroxylamine. The title compound was obtained in 72.6% yield as white crystals, m.p. 87.3° C. (Rf =0.43 on a silica gel plate using hexanes:EtOAc, 2:1, v:v, as an eluant). The title compound was prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-benzyloxybenzaldehyde (20 g, 94.23 mmol), N-cyclopentylhydroxylamine (14.3 g, 141.34 mmol), molecular sieves (60 g, 4A) and silica gel (15 g) in chloroform (300 mL) was stirred at room temperature under argon atmosphere for 48 hrs and then was refluxed for an additional 3 hrs. The mixture was filtered and rotary evaporated to give crystals which were recrystallized from hexanes and EtOAc to provide the title compound as white crystals, 23.7 g, 85.1 % yield), m.p. 115.1 ° C. (Rf =0.35 on a silica gel plate using hexanes:EtOAc, 1:1, v:v, as an eluant). was refluxed for an additional 3 hrs The mixture was filtered rotary evaporated to give crystals which were recrystallized from hexanes and EtOAc

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Ethoxybenzaldehyde (22.0 g, 0.1467 mol) and N-cyclopentylhydroxylamine (14.1 g, 0.1398 mol) were mixed into toluene (200 mL) with p-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol). The mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap to remove generated water. The solution was rotary evaporated to give a residue which was purified by flash chromatography over silica gel with EtOAc as an eluant and then recrystallization from a mixed solvent of hexanes and EtOAc. The title compound was obtained as a solid (21.24 g 65.1% yield), m.p. 95.1° C. (Rf =0.18 on a silica gel plate using hexanes:EtOAc, 2:1, v/v, as an eluant). The mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap to remove The solution was rotary evaporated to give a residue which was purified by flash chromatography over silica gel with EtOAc as an eluant recrystallization from a mixed solvent of hexanes and EtOAc

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Ethoxybenzaldehyde (22.0 g, 0.1467 mol) and N-cyclopentylhydroxylamine (14.1 g, 0.1398 mol) were mixed into toluene (200 mL) with p-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol). The mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap to remove generated water. The solution was rotary evaporated to give a residue which was purified by flash chromatography over silica gel with EtOAc as an eluant and then recrystallization from a mixed solvent of hexanes and EtOAc. The title compound was obtained as a solid (21.24 g 65.1% yield), m.p. 95.1° C. (Rf =0.18 on a silica gel plate using hexanes:EtOAc, 2:1, v/v, as an eluant). The mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap to remove The solution was rotary evaporated to give a residue which was purified by flash chromatography over silica gel with EtOAc as an eluant recrystallization from a mixed solvent of hexanes and EtOAc