Water → (2S)-tert-butyl 4-hydroxy-2-(((triisopropylsilyl)oxy)methyl)piperidine-1-carboxylate

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Reaction Conditions

Reaction Steps

Chlorotriisopropylsilane (2.284 g, 11.85 mmol) was added dropwise to a 0° C. solution of Example 260A (2.65 g, 10.77 mmol), triethylamine (1.253 g, 12.39 mmol) and 4-(dimethylamino)pyridine (0.263 g, 2.154 mmol) in dichloromethane (25 mL). The mixture was stirred at 0° C. for 20 minutes and at room temperature for 16 hours. Water (50 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (twice), and the combined extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (gradient of 0-30% ethyl acetate/heptanes) to give the title compound as a mixture of diastereomers. MS (ESI+) m/z 388.0 (M+H)+.

Provenance & Evidence