Citric Acid → Tert-butyl 3-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)piperidine-1-carboxylate

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Reaction Steps

A solution of 1-tert-butyl 3-methyl 5-(tert-butyldimethylsilyloxy)piperidine-1,3 from step A in THF (100 mL) was treated with LiBH4 (0.84 g, 38.5 mmol) at 0° C. stirring for 2 hours, warmed to room temperature, and then treated with citric acid (1M) till pH=4. The volatiles were removed in vacuo, and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. MS (m/z): 246 (M-Boc+H)+.

Provenance & Evidence