[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1([C:15](O)=[O:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1([CH2:15][OH:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1Lithium aluminum hydride powder (15.62 g., 0.412 mole) in dry tetrahydrofuran (THF) (600 ml.) was heated under reflux for 15 minutes, after which 4-amino-1-methylpiperidine-4-carboxylic acid (31.0 g., 0.196 mole) in the form of a dry powder was added portionwise under nitrogen, with efficient stirring. After the addition was completed, the reaction mixture was heated under reflux for four hours, cooled to 0° C. under nitrogen with efficient stirring, worked up by careful slow addition of water (20 ml.), 15% aqueous NaOH (20 ml.) and again water (10 ml.). The reaction mixture was filtered and the precipitate was extracted with boiling THF (3 ×150 ml.). The THF liltrate and the extracts were combined and the solvent removed at 25 mm to give a yellow viscous oil (28.0 g., 98.9% yield).
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