Hydrochloric Acid → HCID 13315050, compound

2-Hydroxymethyl-2,5-diaminopentanoic acid hydrochloride (5 g or 2.5×10-2 mole) is suspended in 75 ml of absolute methanol and the solution is saturated with dry hydrogen chloride. The homogenous solution is then heated under reflux for 48 hours. The reaction mixture is regularly saturated with dry hydrogen chloride. The solvent is evaporated under reduced pressure and the hygroscopic residue is dried under high vacuo (6.2 g) and identified as dihydrochloride of 2-hydroxymethyl-2,5-diaminopentanoic acid methyl ester by NMR. The ester (6.2 g) is dissolved in 100 ml of absolute methanol and 175 ml of a methanolic solution of sodium methylate (1.15 g of Na or 5×10-2 mole) is added. The reaction mixture is stirred at room temperature under nitrogen for 24 hours. The solvent is evaporated under reduced pressure and the residue is extracted many times with hot chloroform to yield analytically pure 3-hydroxymethyl-3-amino-2-piperidone (2.9 g) (yield 81%), m.p. 145° C.

1. temperatureThe homogenous solution is then heated
2. temperatureunder reflux for 48 hours
3. customThe solvent is evaporated under reduced pressure
4. customthe hygroscopic residue is dried under high vacuo (6.2 g)
5. dissolutionThe ester (6.2 g) is dissolved in 100 ml of absolute methanol
6. customThe solvent is evaporated under reduced pressure
7. extractionthe residue is extracted many times with hot chloroform

ORD record

ord-a9390e17d1604edcb44f179533f92db6

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04496588