[NH2:1][CH:2]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:3][C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[NH2:1][CH:2]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH2:12]1)[CH2:3][CH2:4][OH:5]A solution of ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoate (5 g prepared as described in Example 137) in ether (25 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (3 g) in ether (50 ml). The mixture was heated under reflux for 3 hours, allowed to stand for 16 hours with no heating and then heated under reflux for a further 6 hours. Water (3 ml) was added dropwise with stirring to the cooled reaction mixture followed by 15% aqueous sodium hydroxide solution (3 ml) and water (9 ml). The reaction mixture was filtered and the residue washed with ether. The filtrate and the washings were combined, washed with water then brine and dried. Evaporation of the solvent gave a residue which was recrystallised from petroleum ether (b.p. 40°-60° C.) to give 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propan-1-ol (m.p. 98°-99° C.).
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