[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:15]2([NH:24][C:18]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C1COCC1.O>[CH:18]1([NH:24][C:15]2([CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1To a solution of LiAlH4 (0.93 g, 24.4 mmol) and AlCl3 (3.24 g, 24.4 mmol) in THF at 4° C. was added dropwise a solution of 14-aza-7-oxadispiro[4.2.5.1]tetradecane (2.38 g, 12,2 mmol) in THF (15 mL). The resulting mixture was warmed to 20° C. and stirred for 45 min., then cooled to 4° C. Water (5 mL) was slowly added to quench the reaction and a 1N NaOH solution (85 mL) was added to dissolve the resulting solids. The resulting solution was extracted with Et2O (200 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane 1.89 g (79%): GC-MS m/z 197 (M+).
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