[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C@H:19]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[CH2:20][C:21](OC)=[O:22])=[O:17])([CH3:14])([CH3:13])[CH3:12].CO.Cl>ClCCl>[F:31][C:27]1[CH:26]=[C:25]([C@@H:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:20][CH:21]=[O:22])[CH:30]=[CH:29][CH:28]=1Diisobutylaluminium hydride (1 M in dichloromethane, 39 ml, 39 mmol) was cooled to −78° C. and added dropwise to a solution of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoate (WO0039125, p 60, preparation 12) (5.4 g, 18.2 mmol) in dichloromethane (100 ml) at −78° C. The reaction was stirred for 30 minutes at −78° C., then methanol (50 ml, pre-cooled to −78° C.) was added. The reaction was stirred for 30 minutes, then 2 N hydrochloric acid (250 ml) added. The bi-phasic mixture was allowed to warm up to room temperature, the layers were separated, and the organic layer was dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a clear, colourless oil, 4.8 g.
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