2-(3-ethoxyphenyl)ethanamine

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: 0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.245 ml of 3-ethoxyphenethyl-amine (1.5 mmol) were dissolved in 5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added and after 10 min stirring at rt, the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 ml 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue, 461 mg of a light yellow oil, was not further purified and used directly in the next step. were refluxed for 2 h After cooling down to rt stirring at rt the reaction mixture was then refluxed for 3 h After cooling down to rt concentrated in vacuo The residue was diluted with water/EtOAc After separation of the organic phase the aqueous phase was extracted with EtOAc the combined organic phases were washed with brine dried with magnesium sulfate filtered off concentrated in vacuo The residue, 461 mg of a light yellow oil, was not further purified

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 from 3-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) and 3-ethoxyphenethylamine, using a similar method to that of preparation 158, in 67% yield. of preparation 158

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(3-ethoxy-phenyl)-ethylamine (7.0 g, 42 mmol) and 37% aqueous formaldehyde solution (3.5 mL) was heated at 110° C. for 30 minutes. The stirring was stopped and the upper water layer was removed by pipette. To the resulting mixture water (5.25 mL) and concentrated HCl (10.5 mL) were added followed by heating 100° C. for 30 minutes. After allowing to cool to room temperature the mixture was evaporated to dryness and recrystallised from acetone yielding the subtitled compound as a cream solid (2.73 g). MH+ 178. 1H NMR δ (DMSO) 1.27-1.35 (3H, t), 2.88-3.03 (2H, t), 3.18-3.40 (2H, br, t), 3.95-4.08 (2H, q), 4.10-4.22 (2H, m), 6.74-6.85 (2H, m), 7.05-7.15 (1H, m), 9.33-9.55 (2H, br.s). the upper water layer was removed by pipette To the resulting mixture water (5.25 mL) and concentrated HCl (10.5 mL) were added by heating 100° C. for 30 minutes to cool to room temperature the mixture was evaporated to dryness recrystallised from acetone yielding the subtitled compound as a cream solid (2.73 g)

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

Procedure: To a solution of LiAlH4 (1M in THF, 13 mL) was added dropwise a solution of 1-ethoxy-3-(2-nitro-ethyl)-benzene (0.5 g, 2.6 mmol) in THF (8 mL). The mixture was refluxed for two hours before allowing to cool and adding dropwise to rochelles salt. The mixture was extracted with ethyl acetate, dried with sodium sulfate and evaporated to dryness. The resulting yellow oil was purified by chromatography on silica, eluting with 3 to 15% MeOH/NH3 in dichloromethane, yielding the subtitled compound as a yellow oil (0.23 g). The mixture was refluxed for two hours to cool adding dropwise to rochelles salt The mixture was extracted with ethyl acetate dried with sodium sulfate evaporated to dryness The resulting yellow oil was purified by chromatography on silica eluting with 3 to 15% MeOH/NH3 in dichloromethane

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

Procedure: 0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.245 ml of 3-ethoxyphenethyl-amine (1.5 mmol) were dissolved in 5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added and after 10 min stirring at rt, the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 ml 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue, 461 mg of a light yellow oil, was not further purified and used directly in the next step. were refluxed for 2 h After cooling down to rt stirring at rt the reaction mixture was then refluxed for 3 h After cooling down to rt concentrated in vacuo The residue was diluted with water/EtOAc After separation of the organic phase the aqueous phase was extracted with EtOAc the combined organic phases were washed with brine dried with magnesium sulfate filtered off concentrated in vacuo The residue, 461 mg of a light yellow oil, was not further purified