[C:1]([S:5][C:6]1[C:7]([C:12](O)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[BH4-].[Li+].[OH-].[Na+]>O1CCCC1.O.C(OCC)(=O)C.CO>[C:1]([S:5][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]To a suspension of 3-t-butylthio-2-carboxypyridine (10.0 g, 47.4 mmol) in tetrahydrofuran (200 mL) cooled to −5° C. was added trethylamine (8.25 mL, 47.4 mmol) followed by addition of ethyl chloroformate (4.38 g, 47.4 mmol) and reaction was stirred for 30 min at 0° C. Lithium borohydride (2.58 g, 118 mmol) was added in portions, maintaining the temperature below 5° C. After the addition was complete the reaction was allowed to warm to room temperature and stirred for 1 hour. Temperature was lowered to −5° C. and methanol (10 mL) was added followed by addition of aqueous sodium hydroxide (10 mL, 10%). After addition of ethyl acetate (50 mL) and water (40 mL) dilute hydrochloric acid was added to pH=5.0.
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