[N:1]([C:4]([CH3:15])([CH3:14])[CH2:5][C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=O)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:15][C:4]([NH2:1])([CH3:14])[CH2:5][CH2:6][NH:8][CH2:9][C:10]([F:11])([F:12])[F:13]3-Azido-3-methyl-N-(2,2,2-trifluoroethyl)butanamide (10.9 g, 48.4 mmol) was dissolved into anhydrous THF (50 mL) and added dropwise to a suspension of LAH (3.67 g, 2.0 equiv, 96.8 mmol) in anhydrous THF (200 mL) to maintain the reaction at reflux (30 min). After complete addition, the flask was fitted with a condenser and the reaction heated in a 70° C. oil bath for 8 h. The reaction mixture was cooled in an ice bath and water (4 mL) was added dropwise over 20 min. Then 15% NaOH solution (4 mL) was added dropwise over 10 min. The suspension was stirred for a further 10 min and water (4 mL) was added in one portion and the mixture stirred for 30 min to a give fine white suspension. The suspension was filtered through a pad of Celite® and washed with isopropyl alcohol (2×200 mL). Aqueous acid (6 N HCl, 10.0 mL) was added to the combined filtrate and concentrated on a rotovap to an oily residue. The residue was partitioned between DCM (100 mL) and water (100 mL). The aqueous layer was adjusted to pH ˜14 and the organic layer was separated and the aqueous phase was extracted with DCM (2×50 mL). The combined organic layers were combined and dried over anhydrous MgSO4, filtered and concentrated with a bath temperature between 10-13° C. to an orange liquid (8.84 g, quant). 1H NMR (CDCl3, 400 MHz): δ 1.15 (s, 6H), 1.55-1.62 (t, J=7.2, 2H), 2.81-2.86 (t, J=7.2, 2H) 3.15-3.22 (q, J=9.6, 2H). LRMS (ESI+) for C7H15F3N2 (184.1); Found: 185 (MH+).
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