(2S)-2-benzyl-1-methylpiperazine

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

Procedure: Prepared from 5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indole-3-propanoic acid (Description 12) and (2S)-1-methyl-2-(phenylmethyl)piperazine (Description 35) according to the method of Description 25. 1H NMR (400 MHz, CDCl3) mixture of two amide rotamers; δ7.56-6.98 (12H, m), 4.09, 3.93 (total 1H, each d, J 13.1 Hz), 3.53, 3.47 (total 3H, each s), 3.20-1.98 (12H, m), and 2.39, 2.38 (total 3H, each s). m/z (ES+) 520, 522 (M+1).

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

Procedure: Prepared from 5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indole-3-propanoic acid (Description 12) and (2S)-1-methyl-2-(phenylmethyl)piperazine (Description 35) according to the method of Description 25. 1H NMR (400 MHz, CDCl3) mixture of two amide rotamers; δ7.56-6.98 (12H, m), 4.09, 3.93 (total 1H, each d, J 13.1 Hz), 3.53, 3.47 (total 3H, each s), 3.20-1.98 (12H, m), and 2.39, 2.38 (total 3H, each s). m/z (ES+) 520, 522 (M+1).

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminium hydride (1.0M in ether, 20.2 mL, 20.2 mmol) was added to a stirred, cooled (0° C.) suspension of (6S)-1-methyl-6-(phenylmethyl)-2,5-piperazinedione (Description 34, 1.1 g, 5.0 mmol) in THF (60 mL) and the mixture was heated under reflux for 1 h. The mixture was cooled to −20° C. and saturated aqueous sodium sulfate (20.2 mL) was added. The mixture was stirred at room temperature for 15 min., filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2C2/MeOH/NH3(aq.) (90:10:1), to give the title compound as a yellow oil (0.83 g, 87%). 1H NMR (250 MHz, CDCl3) δ7.31-7.15 (5H, m), 3.17 (1H, dd, J 13.3, 3.9 Hz), 2.92-2.70 (4H, m), 2.46 (2H, m), 2.43 (3H, s), 2.27 (2H, m) and 1.51 (1H, br s). m/z (ES+) 191 (M+1). cooled the mixture was heated under reflux for 1 h filtered the solvent was evaporated under reduced pressure The residue was purified by flash column chromatography on silica gel eluting with CH2C2/MeOH/NH3(aq.) (90:10:1)

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

Procedure: Prepared from 5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indole-3-propanoic acid (Description 12) and (2S)-1-methyl-2-(phenylmethyl)piperazine (Description 35) according to the method of Description 25. 1H NMR (400 MHz, CDCl3) mixture of two amide rotamers; δ7.56-6.98 (12H, m), 4.09, 3.93 (total 1H, each d, J 13.1 Hz), 3.53, 3.47 (total 3H, each s), 3.20-1.98 (12H, m), and 2.39, 2.38 (total 3H, each s). m/z (ES+) 520, 522 (M+1).

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminium hydride (1.0M in ether, 20.2 mL, 20.2 mmol) was added to a stirred, cooled (0° C.) suspension of (6S)-1-methyl-6-(phenylmethyl)-2,5-piperazinedione (Description 34, 1.1 g, 5.0 mmol) in THF (60 mL) and the mixture was heated under reflux for 1 h. The mixture was cooled to −20° C. and saturated aqueous sodium sulfate (20.2 mL) was added. The mixture was stirred at room temperature for 15 min., filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2C2/MeOH/NH3(aq.) (90:10:1), to give the title compound as a yellow oil (0.83 g, 87%). 1H NMR (250 MHz, CDCl3) δ7.31-7.15 (5H, m), 3.17 (1H, dd, J 13.3, 3.9 Hz), 2.92-2.70 (4H, m), 2.46 (2H, m), 2.43 (3H, s), 2.27 (2H, m) and 1.51 (1H, br s). m/z (ES+) 191 (M+1). cooled the mixture was heated under reflux for 1 h filtered the solvent was evaporated under reduced pressure The residue was purified by flash column chromatography on silica gel eluting with CH2C2/MeOH/NH3(aq.) (90:10:1)