[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][C@H:17]([CH3:19])[C@H:16]([C:20]#[N:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>C(OCC)C>[CH2:7]([N:14]1[CH2:18][C@H:17]([CH3:19])[C@H:16]([CH2:20][NH2:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Lithium aluminum hydride (80%, 3.89 g) was suspended in diethyl ether (90 mL). While the suspension was cooled on an ice bath, a diethyl ether solution (25 mL) of cis-1-benzyl-4-methyl-3-pyrrolidinecarbonitrile (4.11 g) was added dropwise and the mixture was stirred at room temperature for 1 hour. While the reaction mixture was cooled on an ice bath, a saturated aqueous solution of sodium hydrogen carbonate (8 mL) was carefully added dropwise. Following dilution with diethyl ether (100 mL), insoluble materials were collected by filtration and were washed with diethyl ether. The filtrate and the washing solution were combined and the combined solution was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (hexane:ethyl acetate=1:1 shifted to ethyl acetate: methanol=10:1) to give 2.35 g of cis-1-benzyl-4-methyl-3-aminomethylpyrrolidine as a pale yellow oil.
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