[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH:14]3[NH2:21])[CH2:12]1)[CH2:18]2)=O>C1COCC1>[NH2:21][CH:14]1[CH:13]2[CH2:12][C:11]3([CH2:9][OH:8])[CH2:18][CH:17]([CH2:16][CH:15]1[CH2:20]3)[CH2:19]2Lithium aluminium hydride (5 g, 135 mmol) was added to a solution of 4-aminoadamantane-1-carboxylic acid methyl ester (5 g, 23.9 mmoles) in dry THF (100 ml) at 0-5° C. and the mixture heated under reflux for 3 h. It was then cooled to 0° C. and quenched with water (10 ml) followed by NaOH solution (20%, 12.5 ml). After stirring for 30 min, it was filtered through hyflo bed to remove inorganics. The clear filtrate was concentrated under reduced pressure and the residue triturated with hexane to give 4-amino-1-hydroxymethyladamantane (3.9 g, 90%). LC-MS (m/z): 182 (M+1). 1H NMR (300 MHz, DMSO-d6) δ 3.0 (d, 2H), 2.85 (b. s., 1H), 1.2-2.1 (13H, m).
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