Aluminium lithium hydride → racemic (2'R,3R,4'S)-6-chloro-4'-[5-chloro-2-(1-hydroxymethyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

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To a mixture of LiAlH4 (15 mg, 0.4 mmol) in THF (2 mL) was added racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (RO5247453-000) (60 mg, 0.1 mmol). The mixture was stirred in a ice bath for 1.5 h, quenched with MeOH, purified by Prep-HPLC to give title compound (14 mg, 24%). m/z (M+H)+: 569

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