2-methoxy-4-(pyrrolidin-1-ylmethyl)aniline

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

Procedure: 10% Pd on carbon (12 mg, 0.866 mmol) was added to a solution of 1-(3-methoxy-4-nitrobenzyl)pyrrolidine (Preparation 105, 180 mg, 0.76 mmol) in EtOH (3 mL). The reaction mixture was degassed and then stirred for 1 hour at room temperature under an atmosphere of hydrogen. The reaction was filtered on a pad of Celite and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel column chromatography eluting with 5% methanol in dichloromethane to afford the title compound as a colourless oil (0.12 g, 76.3%). 1H-NMR (500 MHz, CDCl3): δ 1.79 (t, J=6.7 Hz, 4H), 2.5 (t, J=6.7 Hz, 4H), 3.53 (s, 2H), 3.75 (s, br, 2H), 3.86 (s, 3H), 6.65 (d, J=9.3 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 6.81 (d, J=1.5 Hz, 1H). The reaction mixture was degassed The reaction was filtered on a pad of Celite the filtrate was concentrated under reduced pressure The residue was purified on silica gel column chromatography eluting with 5% methanol in dichloromethane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the product of Example 49A (220 mg, 3.64 mmol) in tetrahydrofuran (20 mL) at 0° C. was added borane tetrahydrofuran complex (18 mL, 18 mmol) and the mixture was stirred at 0° C. for 2 hours and at 60° C. for 4 hours. After cooling to ambient temperature, methanol (20 mL) was added and stirring was continued for 30 minutes. The organic phase was concentrated and the residue was purified via preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. MS: 207 (M+H+). After cooling to ambient temperature stirring was continued for 30 minutes The organic phase was concentrated the residue was purified via preparative HPLC