[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]([NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([CH3:30])[CH2:26][CH2:25]2)=O)[CH:16]=[CH:17][CH:18]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][NH:23][C@H:24]2[CH2:25][CH2:26][C@H:27]([CH3:30])[CH2:28][CH2:29]2)[CH:16]=[CH:17][CH:18]=11M Lithium aluminium hydride (5 mL, 5 mmol) and dry THF (5 mL) was cooled to 0° C. where upon 98% sulphuric acid (133 μL, 2.5 mmol) was added over a period of 10 min. The resulting solution was stirred for 10 min at 0° C. and then allowed to warm to room temperature over 30 min. 3-(3-Chloro-phenyl)-N-(trans-4-methyl-cyclohexyl)-propionamide (900 mg, 3.2 mmol) in THF (6 mL) was added and the solution stirred for 16 h at room temperature. The reaction was quenched by the sequential addition of water (190 μL), 4N NaOH (190 μL) and water (190 μL). Dilution with THF (25 mL) followed by the addition of MgSO4 (5 g), filtration and concentration in vacuo yielded 700 mg of [3-(3-Chloro-phenyl)-propyl]-(trans-4-methyl-cyclohexyl)-amine.
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