3-[4-(2-methylpropyl)phenyl]propanal

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: Condensation of 15 (1.0 g, 3.6 mmol) and 3-(4-isobutylphenyl)-propionaldehyde (700 mg, 3.6 mmol), following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(4-isobutylphenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (977 mg, 61%), as an off-white solid: mp 162-165° C.; IR (KBr): 2953, 1773, 1498, 1451 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 11.55 (s, 1H), 10.00 (s, 1H), 7.17-7.08 (m, 5H), 7.00 (s, 2H), 3.32-3.28 (m, 1H), 3.21-3.08 (m, 1H), 3.08-2.95 (m, 1H), 2.70 (d, J=5 Hz, 3H), 2.65-2.52 (m, 3H), 2.41 (d, J=7 Hz, 2H), 2.14-1.73 (m, 7H), 1.68-1.49 (m, 4H), 0.85 (d, J=7 Hz, 6H); HRMS-API (m/z): [M+H]+ calcd for C27H36N2O2, 421.2855; found, 421.2858; HPLC: method A, 7.49 minutes (>99%); method B, 13.59 minutes (>99%); Anal. Calcd for C27H36N2O2.HCl.0.5H2O: C, 69.58; H, 8.22; N, 6.01. Found: C, 69.23; H, 8.20; N, 5.87.

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

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

Procedure: 4-Isobutyl cyclohexanepropanal was similarly prepared as described in Examples I and II. First, 4-isobutyl benzaldehyde (600 g, commercially available from Mitsubishi Gas Chemical America, Inc.) was used to obtain 3-(4-isobutyl-phenyl)-propionaldehyde (568 g) with a boiling point of 119° C. at a pressure of 5 mmHg 3-(4-Isobutyl-phenyl)-propionaldehyde (400 g) was consequently used to provide 4-isobutyl cyclohexanepropanal (245 g) with a boiling point of 107° C. at a pressure of 4.4 mmHg

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

Procedure: 4-Isobutyl 1-(3-methoxy-2-propen-1-yl)benzene was similarly prepared as described in Examples I and II. First, 4-isobutyl benzaldehyde (600 g, commercially available from Mitsubishi Gas Chemical Company, Inc.) was used to obtain 3-(4-isobutyl-phenyl)-propionaldehyde (568 g) with a boiling point of 119° C. at a pressure of 5 mmHg. 3-(4-Isobutyl-phenyl)-propionaldehyde (345 g) was consequently used to provide 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene (188 g) with a boiling point of 124° C. at a pressure of 4 mmHg.

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

Procedure: 4-Isobutyl cyclohexanepropanal was similarly prepared as described in Examples I and II. First, 4-isobutyl benzaldehyde (600 g, commercially available from Mitsubishi Gas Chemical Company, Inc.) was used to obtain 3-(4-isobutyl-phenyl)-propionaldehyde (568 g) with a boiling point of 119° C. at a pressure of 5 mmHg. 3-(4-Isobutyl-phenyl)-propionaldehyde (400 g) was consequently used to provide 4-isobutyl cyclohexanepropanal (245 g) with a boiling point of 107° C. at a pressure of 4.4 mmHg.

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

Procedure: Condensation of 15 (1.0 g, 3.6 mmol) and 3-(4-isobutylphenyl)-propionaldehyde (700 mg, 3.6 mmol), following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(4-isobutylphenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (977 mg, 61%), as an off-white solid: mp 162-165° C.; IR (KBr): 2953, 1773, 1498, 1451 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 11.55 (s, 1H), 10.00 (s, 1H), 7.17-7.08 (m, 5H), 7.00 (s, 2H), 3.32-3.28 (m, 1H), 3.21-3.08 (m, 1H), 3.08-2.95 (m, 1H), 2.70 (d, J=5 Hz, 3H), 2.65-2.52 (m, 3H), 2.41 (d, J=7 Hz, 2H), 2.14-1.73 (m, 7H), 1.68-1.49 (m, 4H), 0.85 (d, J=7 Hz, 6H); HRMS-API (m/z): [M+H]+ calcd for C27H36N2O2, 421.2855; found, 421.2858; HPLC: method A, 7.49 minutes (>99%); method B, 13.59 minutes (>99%); Anal. Calcd for C27H36N2O2.HCl.0.5H2O: C, 69.58; H, 8.22; N, 6.01. Found: C, 69.23; H, 8.20; N, 5.87.

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