[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][CH:9]1[C:16]([O-:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([NH2+]C(C1C=CC=CC=1)C)C1C=CC=CC=1.Cl.[Na+].[Cl-]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:12][CH2:13]2)[CH2:10][CH:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]To a suspension of N-benzyl-1-phenylethanaminium 6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylate (single unknown enantiomer) (D2) (10 g, 24 mmol) in EtOAc (100 mL) stirred at 0° C. was slowly added aqueous HCl 0.5N (100 ml) saturated with NaCl. After addition was completed, dissolution was observed. The organic layer was decanted, washed with saturated NaCl, dried (Na2SO4) and evaporated in vacuo to afford 5 g of acid which was recrystallized from petroleum ether/EtOAc (60 ml/20 ml) to afford the tile compound (D3) (2.8 g) as white solid.
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