Methane → 3-Hydroxy-2-hydroxymethylpiperidine

A mixture of 20.0 g (105 mmol) 3-hydroxy-2-(hydroxymethyl)-pyridine hydrochloride, 4.0 g (18 mmol) platinum(IV) oxide, 4 g charcoal (Norit SX1) and 300 ml acetic acid was stirred at room temperature for 20 h under a hydrogen pressure of 10 bar in an autoclave. The catalyst was filtered off and washed with acetic acid. The filtrate was concentrated in vacuo, redissolved in isopropanol and treated with 29.0 g (210 mmol) potassium carbonate. After stirring for 30 min. the mixture was filtered, and the solvent was evaporated in vacuo to give 15.7 g of crude (2RS,3RS)-2-hydroxymethyl-piperidin-3-ol. A portion of 2.0 g of the crude intermediate was dissolved in 50 ml dichloromethane and treated with 5.2 ml (30 mmol) N,N-diisopropylethylamine and 2.4 ml (16 mmol) benzyl chloroformate at 0° C. After 45 min. water and saturated ammonium chloride solution were added. The mixture was extracted with four portions of dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash chromatography gave 0.82 g (23% based on 3-hydroxy-2-(hydroxymethyl)-pyridine hydrochloride) of the title compound as an off-white oil.

1. filtrationThe catalyst was filtered off
2. washwashed with acetic acid
3. concentrationThe filtrate was concentrated in vacuo
4. dissolutionredissolved in isopropanol
5. stirringAfter stirring for 30 min. the mixture
6. filtrationwas filtered
7. customthe solvent was evaporated in vacuo

ORD record

ord-b09a9b9f9fd14ce2a50cddda206fab90

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07939533B2