[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([NH:11][CH2:12][CH2:13][C:14]#[N:15])[CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O>[CH:7]1([NH:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:10][CH2:9][CH2:8]1To a cooled (0° C.) suspension of lithium aluminum hydride (3.056 g, 80.5 mmol) in anhydrous diethyl ether (120 mL) was added a solution of 3-(cyclobutylamino)propanenitrile (5.000 g, 40.3 mmol) in anhydrous diethyl ether (40 mL), dropwise over 45 mins. The reaction mixture was stirred at room temperature for 15 mins and at reflux for 4 hrs, cooled to room temperature and stirred for 1 hr. The mixture was cooled to 0° C. and vigorously stirred while water (3.1 mL) was added dropwise, followed by 15% aqueous sodium hydroxide (3.1 mL), and finally water (9.3 mL). The resultant slurry was warmed to room temperature, stirred for 15 mins, and anhydrous magnesium sulfate added, stirring for an additional 15 mins. Solid materials were removed by filtration, washing multiple times with warm methylene chloride, and the filtrate concentrated under reduced pressure to give the desired product as a pale yellow liquid (3.44 g, 66%). 1H NMR (CDCl3, 300 MHz) 3.14 (m, 1H), 2.69-2.62 (m, 2H), 2.53-2.45 (m, 2H), 2.13-2.10 (m, 2H), 1.56-1.48 (m, 6H), 1.33 (br s, 3H).
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