Reaction Steps
A solution of intermediate (S)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-(2-methyl-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (215 mg, 0.447 mmol) in 1,4-dioxane (2 mL) was then treated with a 4 N solution of hydrogen chloride (4 mL) and stirred for 2 h. The reaction was then evaporated to a colorless solid, suspended in EtOAc (10 mL), and washed with a saturated aqueous K2CO3 solution (3 mL) followed by brine (3 mL). The organic portion was then dried over MgSO4, filtered, and evaporated to afford the title compound as a burgundy colored oil (127 mg, 75%). 1H NMR (CDCl3) 7.26-7.11 (m, 4H), 6.78 (d, J=8.8, 1H), 6.53 (d, J=2.9, 1H), 6.43 (dd, 8.7, 2.6, 1H), 4.74-4.71 (m, 1H), 3.78 (s, 3H), 3.39-3.35 (m, 2H), 3.16-3.08 (m, 2H), 2.96 (td, J=11.2, 2.9, 1H), 2.87-2.70 (m, 2H), 2.56-2.49 (m, 1H), 2.36 (s, 3H), 1.92-1.72 (m, 6H), 1.61-1.57 (m, 2H). 13C NMR 148.4, 146.5, 144.8, 136.7, 136.4, 130.7 (CH), 130.2 (CH), 126.8 (CH), 126.1 (CH), 113.3 (CH), 108.6 (CH), 106.8 (CH), 80.6, (CH), 56.8 (CH2), 56.8 (CH3), 55.3 (CH), 51.3 (CH2), 46.0 (CH2), 37.9 (CH2), 32.97 (CH2), 24.2 (CH2), 19.8 (CH3). LC/MS (Method A) 5.03 min, [M+1]+ 381.
