Sodium Hydroxide → 2-Amino-3,3-diphenylpropan-1-ol

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Reaction Steps

To a solution of 1M-lithium aluminium hydride in diethyl ether (40ml) was added β,β-diphenylalanine hydrochloride (3.70g, Example 1b) over a period of 1h. The solution was heated at reflux for 1h, cooled to room temperature and to the solution was cautiously added 2M-sodium hydroxide (40ml). After filtering the solution through Celite, the residue was washed with ethyl acetate and the organic phase of the combined filtrates was washed with water, saturated brine and dried (MgSO4). The solid which formed on removal of the solvent in vacuo was washed with hexane to give 2-amino-3,3-diphenylpropan-1-ol 2.52g, mp 107°-8° C. 1H NMR (360MHz, CDCl3) d 7.36-7.14 (10H, m), 3.79 (1H, d, J=10.5Hz), 3.6 (1H, m), 3.57 (1H, dd, J=10.7Hz and 3.3Hz), 3.31 (1H, dd, J=10.7Hz and 6.7Hz), m/z (CI+) 228 (M+H).

Provenance & Evidence