(2-phenylcyclopentyl)methanamine

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

Procedure: A solution of 2-phenylcyclopentane carboxamide (900 mg, 4.76 mmol) in THF (15 mL) was added dropwise to a cold (0° C.) suspension of LAH (271 mg, 7.13 mmol) in THF (15 mL). The cooling bath was removed and the mixture was stirred for 2.5 h. The reaction was quenched with MeOH (2 mL) and then 1N HCl (2 mL). The mixture was filtered through Celite. The filtrate was diluted with EtOAc and washed with sat'd sodium bicarbonate (3×), washed with brine, dried over potassium carbonate. and concentrated to give (2-phenylcyclopentyl)methanamine as a clear oil. (760 mg, 91.2%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.37-7.14 (m, 5H), 2.76 (dd, J=12.5, 4.8 Hz, 1H), 2.67-2.51 (m, 2H), 2.18-1.96 (m, 3H), 1.92-1.65 (m, 3H), 1.53-1.33 (m, 3H). LCMS: M+1=176.18. The cooling bath was removed The reaction was quenched with MeOH (2 mL) The mixture was filtered through Celite The filtrate was diluted with EtOAc washed with sat'd sodium bicarbonate (3×) washed with brine dried over potassium carbonate and concentrated