[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([CH2:18][NH2:19])[CH2:17][CH2:16][CH2:15]1Add LiAlH4 (461 mg, 12.1 mmol) to a solution of 1-(2-fluoro-phenyl)-cyclobutanecarbonitrile (1.38 g, 7.88 mmol) in dimethoxyethane (30 mL). Stir the solution at reflux overnight then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with CH2Cl2 (3×30 mL). Combine the organic extracts and wash with additional aq satd Rochelle's salt solution (30 mL) and brine (30 mL). Dry, filter and concentrate the organic solution then purify the crude material by flash chromatography, using 20% MeOH/CH2Cl2, to give the title compound (1 g, 71%) as a white solid. MS (ES) 180.1 (M+1)+.
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