3-phenylbutanal

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: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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: In an analogous manner to Example 117, 1-{(1S-2-[4-(3-phenylbutyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol dihydrochloride was prepared from 3-phenylbutyraldehyde and 1-{(1S)-2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol (See Example 243). HRMS: calcd for C29H39F3N2O2, 504.29636; found (ESI, [H+M]+), 505.3025. [α]D25=−12° (c=0.0091 g/mL, MeOH); CD=+@268 nm.

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

Procedure: [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-triphenyl-phosphonium bromide (0.2678 g, 0.451 mmol) was dissolved in THF (2.7 mL) at 0° C. Potassium tert-butoxide (1 M in THF, 0.5 mL, 0.50 mmol) was added and after stirring 15 minutes 3-phenyl-butyraldehyde (0.074 mL, 0.50 mmol) was added and the ice bath was removed. After 15 minutes, analytical LCMS indicated complete reaction. Standard aqueous workup followed by silica gel chromatography (0-20% EtOAc in hexanes) afforded the title compound. was added the ice bath was removed reaction

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

Procedure: 1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.1 g, 0.27 mmol), 3-phenyl-butyraldehyde (0.048 g, 0.33 mmol) and sodium triacetoxyborohydride (0.11 g, 0.54 mmol) were mixed in CH2Cl2 and stirred overnight. Lithium hydroxide monohydrate (0.100 g, 2.38 mmol) in MeOH/H2O was added and the reaction stirred at 60° C. for 1 hour. The reaction was submitted to standard aqueous workup to yield the title compound. the reaction stirred at 60° C. for 1 hour

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

Procedure: To a mixture of 3-phenylbutyraldehyde (10.0 g, 67.5 mmol, 1.0 equiv) and benzene (150 ml) and silica gel (5 g) was added N-tert-butylhydroxylamine (7.22 g, 81.0 mmol, 1.2 equiv) and the mixture stirred at rt for 18 h. The mixture was filtered and the filtrate was concentrated under vacuum to give N-tert-butyl-C-(2-phenylpropyl)nitrone (13.74 g, 92.80%) as a light yellow oil. 1H NMR (CDCl3) δ 7.33–7.19 (m, 5H), 6.65 (t, 1H), 3.18–3.04 (m, 1H), 2.90–2.65 (m, 2H), 1.40 (s, 9H), 1.34–1.32 (d, 3H). The mixture was filtered the filtrate was concentrated under vacuum