1-N-Boc-4-Piperidinecarboxylic acid methyl ester → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (171.3 mmol, 1 eq) in THF (250 ml) was added LiBH4 (342.6 mmol, 2 eq) at 0° C. The reaction mixture was then heated at reflux for 2 h and then cooled to 0° C. Ice-water (100 g) was added and the aqueous layer was extracted with ethyl acetate (200 ml). The organic layer was washed with brine (50 ml), the layers were separated, and the organics dried over Na2SO4, concentrated and employed in the next step without further purification. Yield: 82%

Provenance & Evidence