Water → [1-(2-Methoxyethyl)piperidin-4-yl]methanol

Participants

Reaction Steps

A solution of (1-(2-methoxyacetyl)piperidin-4-yl)methyl 2-methoxyacetate from the previous step (6.5 g, 25.1 mmol) in THF (10 mL) was added drop-wise to a 1 M solution of LiAlH4 in THF (55.0 mL, 55.0 mmol) under argon. The reaction mixture was stirred at room temperature for 2 days and then cooled to 0° C. Water (2.0 mL) was added drop-wise. A gelatinous white solid formed. 0.2M aq NaOH solution (2.0 mL) was added drop-wise. Water (5.0 mL) was added and the resulting mixture stirred at room temperature for 3 h. The white solid was removed by filtration. The filtrate was concentrated in vacuo and dried on an Isolute HM-N cartridge (eluting with EtOAc). The resulting organic solution was dried in vacuo to give (1-(2-methoxyethyl)piperidin-4-yl)methanol (3.65 mg, 84%) as a yellow oil.

Provenance & Evidence