[F:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH2:16][NH2:17].[BH4-].[Na+].ClCCl>CO.ClCCl.C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([NH:17][CH2:16][CH:15]([OH:14])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]
1-(3-Fluoro-4-methoxyphenyl)propan-2-one (2.73 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (2.58 g) were condensed and subsequently reduced with sodium borohydride (2.0 g) by a procedure analogous to that described in Example 1, except dichloromethane was used instead of ethyl acetate in the work-up. Chromatography of the residue on silica gel in 5% methanol-dichloromethane gave N-[2-(3-fluoro-4-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine, mp 93°-5° C. (diethyl ether) as a 55:45 mixture of diastereoisomers.
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