[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([OH:20])[C@@H:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])=[CH:5][CH:4]=1)[CH3:2].Cl>C(#N)C.O>[NH2:12][C@@H:10]([CH3:11])[C@@H:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[OH:20]To a stirred solution of tert-butyl [(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate (450 mg, 1.51 mmol) in acetonitrile (10 ml) was added aq. HCl (6 N, 3 ml), and stirring was continued for 3.5 h. Then the mixture was diluted with water (10 ml), and acetonitrile was removed in vacuo. The mixture was washed with dichloromethane (20 ml). The aqueous layer was then made alkaline (pH≈10) by addition of aq. NaOH (10 N), and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried with Na2SO4, the solvent was removed in vacuo to afford white solid, 280 mg (97%).
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