(2R)-hexan-2-amine

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

Procedure: 2,2-Dimethoxyacetaldehyde (7.54 mL) was added to a solution of (R)-hexan-2-amine (5.06 g) in methanol (20 mL) and the mixture stirred at ambient temperature for 5 h. A slurry of 10% palladium on carbon (200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 16 h, then filtered and concentrated in vacuo to afford the sub-titled compound as a colourless liquid (9.22 g). 1H NMR (400 MHz, CDCl3) δ 4.46 (t, J=5.5 Hz, 1H), 3.39 (s, 6H), 2.72 (ddd, J=31.1, 11.9, 5.6 Hz, 2H), 2.60 (sextet, J=6.0 Hz, 1H), 1.36-1.24 (m, 6H), 1.04 (d, J=6.2 Hz, 3H), 0.90 (t, J=6.9 Hz, 3H) the mixture hydrogenated at 5 bar for 16 h filtered concentrated in vacuo

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

Procedure: 2,2-Dimethoxyacetaldehyde (7.54 mL) was added to a solution of (R)-hexan-2-amine (5.06 g) in methanol (20 mL) and the mixture stirred at ambient temperature for 5 h. A slurry of 10% palladium on carbon (200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 16 h, then filtered and concentrated in vacuo to afford the sub-titled compound as a colourless liquid (9.22 g). 1H NMR (400 MHz, CDCl3) δ 4.46 (t, J=5.5 Hz, 1H), 3.39 (s, 6H), 2.72 (ddd, J=31.1, 11.9, 5.6 Hz, 2H), 2.60 (sextet, J=6.0 Hz, 1H), 1.36-1.24 (m, 6H), 1.04 (d, J=6.2 Hz, 3H), 0.90 (t, J=6.9 Hz, 3H) the mixture hydrogenated at 5 bar for 16 h filtered concentrated in vacuo

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

Procedure: In a manner analogous to the method described in example 163, {1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-acetic acid was reacted with (R)-(+)-2-aminohexane (Alfa) to give the title product. LC-MS (ES+) 748 [(M+H)+].

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

Procedure: 2,2-Dimethoxyacetaldehyde (7.54 mL) was added to a solution of (R)-hexan-2-amine (5.06 g) in methanol (20 mL) and the mixture stirred at ambient temperature for 5 h. A slurry of 10% palladium on carbon (200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 16 h, then filtered and concentrated in vacuo to afford the sub-titled compound as a colourless liquid (9.22 g). 1H NMR (400 MHz, CDCl3) δ 4.46 (t, J=5.5 Hz, 1H), 3.39 (s, 6H), 2.72 (ddd, J=31.1, 11.9, 5.6 Hz, 2H), 2.60 (sextet, J=6.0 Hz, 1H), 1.36-1.24 (m, 6H), 1.04 (d, J=6.2 Hz, 3H), 0.90 (t, J=6.9 Hz, 3H) the mixture hydrogenated at 5 bar for 16 h filtered concentrated in vacuo