(2R)-2-methylpiperidine

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

Procedure: The title compound was prepared from (R)-2-methyl piperidine using analogous procedures to those described for the preparation of Intermediate 95e. LCMS (Method 3): Rt 3.63 min, m/z 679 [MH+].

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

Procedure: The title compound was prepared from (R)-2-methyl piperidine using analogous procedures to those described for the preparation of Intermediate 95e. LCMS (Method 3): Rt 3.63 min, m/z 679 [MH+].

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-fluoro-3-(trifluoromethyl)benzonitrile (1.0 g, 5.29 mmol) and (R)-(−)-2-methylpiperidine (3.1 mL, 26.4 mmol) was prepared in DMSO (10 mL) and heated at 100° C. under nitrogen for 12 hours. The reaction mixture was diluted with EtOAc, and then washed with water, a saturated aqueous solutions of NaHCO3 and a saturated aqueous solution of NH4Cl. The organic layer was dried (MgSO4) and concentrated under vacuum to give the title compound as a yellow oil, which was used without further purification in the next step. HPLC (Method A) Rt 5.65 min (82.6%). LC/MS (Method B): 269.1 (M+H)+. washed with water The organic layer was dried (MgSO4) concentrated under vacuum

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-fluoro-3-(trifluoromethyl)benzonitrile (1.0 g, 5.29 mmol) and (R)-(−)-2-methylpiperidine (3.1 mL, 26.4 mmol) was prepared in DMSO (10 mL) and heated at 100° C. under nitrogen for 12 hours. The reaction mixture was diluted with EtOAc, and then washed with water, a saturated aqueous solutions of NaHCO3 and a saturated aqueous solution of NH4Cl. The organic layer was dried (MgSO4) and concentrated under vacuum to give the title compound as a yellow oil, which was used without further purification in the next step. HPLC (Method A) Rt 5.65 min (82.6%). LC/MS (Method B): 269.1 (M+H)+. washed with water The organic layer was dried (MgSO4) concentrated under vacuum

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

Procedure: The title compound was prepared from (R)-2-methyl piperidine using analogous procedures to those described for the preparation of Intermediate 95e. LCMS (Method 3): Rt 3.63 min, m/z 679 [MH+].

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

Procedure: The title compound was prepared from (R)-2-methyl piperidine using analogous procedures to those described for the preparation of Intermediate 95e. LCMS (Method 3): Rt 3.63 min, m/z 679 [MH+].

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

Procedure: A solution of 7 g (17.8 mmol) of 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline 8.8 g (88 mmol) of 2-(R)-methylpiperidine in 50 ml of anhydrous chloroform is brought to 60° C. for 6 hours. The reaction mixture is concentrated under vacuum and the residue obtained is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1) to provide 3.8 g of 2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in the form of a colorless oil. (Yield: 45%) The reaction mixture is concentrated under vacuum the residue obtained is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1)

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

Procedure: The title compound was prepared from (R)-2-methyl piperidine using analogous procedures to those described for the preparation of Intermediate 95e. LCMS (Method 3): Rt 3.63 min, m/z 679 [MH+].