Water → 1-Methyl-4-piperidinemethanol

A solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (1.94 g, 9.0 mmol) in THF (15.0 mL) was added drop-wise to a 1M solution of LiAlH4 in THF (13.5 mL, 13.5 mmol) under argon. The reaction mixture was stirred at room temperature for 17 hours and then cooled to 0° C. A mixture of THF and water (1:1 ratio, 1.5 mL) was added drop-wise. A gelatinous white solid formed. 4M aq NaOH solution (0.6 mL) was added drop-wise. Water (2 mL) was added and the resulting mixture stirred at room temperature for 2 hours. The white solid was removed by filtration. The filtrate was loaded onto an Isolute HM-N liquid-liquid extraction column and then eluted with EtOAc (200 mL). The resulting organic phase concentrated in vacuo yielding (1-methylpiperidin-4-yl)methanol as a yellow oil (1.02 g, 88%).

1. temperaturecooled to 0° C
2. additionwas added drop-wise
3. customA gelatinous white solid formed
4. stirringthe resulting mixture stirred at room temperature for 2 hours
5. customThe white solid was removed by filtration
6. extractionThe filtrate was loaded onto an Isolute HM-N liquid-liquid extraction column
7. washeluted with EtOAc (200 mL)
8. concentrationThe resulting organic phase concentrated in vacuo

ORD record

ord-dc2b5761e88d4a67aa06a41de2fd0a16

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093248B2