Water → 4-(2-Hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(2-methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.0 g, 6.5 mmol, 1.0 eq.) in THF (60 mL) was added to a solution of LiAlH4 (490 mg, 13 mmol, 2.0 eq.) in THF (100 mL) at −30° C. The resulting solution was stirred for 1 hour and allowed to warm to 0° C., then stirred for 1 hour at 0° C. Water (0.5 mL) was added dropwise to quench the reaction. The mixture was allowed to warm to room temperature, and 15% NaOH (0.5 mL) and water (1.5 mL) was added. The solids were filtered and the filter cake was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1˜5:1), then by preparative HPLC to yield 4-(2-hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (1.1 g) as a yellow oil.

Provenance & Evidence