Methyl formate → 4-(Hydroxymethyl)piperidine-1-carbaldehyde

4-Piperidinemethanol (10 g, 87 mmol) was dissolved in methyl formate (7 mL, 113 mmol) 0° C., and maintained at that temperature for 30 min, then allowed to reach 20° C. and stirred 90 min. Solid sodium hydroxide was added (0.87 g, pellets) and the mixture was left overnight. Dichloromethane was added, the NaOH removed by filtration and the solution treated with 1M HCl in ether (10 mL). The mixture was filtered through Celite and the solvent was removed under reduced pressure to afford the crude title compound. 1H NMR (400 MHz, CDCl3): 0.85-1.1 (2H, m); 1.55-1.85 (3H, m); 2.5-2.7 (1H, m); 2.95-3.1 (1H, m); 3.3 (2H, d, J 7 Hz); 3.6-3.7 (1H, m); 4.1-4.3 (1H, m); 8 (1H, s).

1. temperaturemaintained at that temperature for 30 min
2. customto reach 20° C.
3. waitthe mixture was left overnight
4. customthe NaOH removed by filtration
5. additionthe solution treated with 1M HCl in ether (10 mL)
6. filtrationThe mixture was filtered through Celite
7. customthe solvent was removed under reduced pressure

ORD record

ord-cba3279ff78b4314b20e4220ed54aa47

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442698B2