(1S)-1-(3-fluorophenyl)ethanamine

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

Procedure: A mixture of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (547 mg, 2.4 mmol), (S)-1-(3-fluorophenyl)ethanamine (500 mg, 3.6 mmol), K2CO3 (662 mg, 4.8 mmol), and KI (797 mg, 4.8 mmol) in anhydrous CH3CN (15 mL) was stirred at rt under N2. Then the solution was refluxed overnight. The solid was filtered off, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC to afford 3-(4-fluorophenyl)-1-((S)-1-(3-fluorophenyl)ethylamino)hex-5-en-3-ol (350 mg, 44%). Then the solution was refluxed overnight The solid was filtered off the solvent was removed under reduced pressure The residue was purified by preparative TLC

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 (S)-1-(3-fluorophenyl)ethylamine (Synquest) to give the title product. LC-MS (ES+) 786 [(M+H)+].

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

Procedure: The title compound was prepared following the same general protocol as described in Step 8-9, Example 1, using the (S)-1-(3-fluorophenyl)ethanamine and the 1-((2′-(tert-butoxycarbonyl)-[1,1′-biphenyl]-4-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid. ESI-MS (m/z): 521 [M+H]+.