Water → 1-(Furan-3-yl)-2-(methylamino)ethan-1-ol

Trimethylsulfonium iodide (20.4 g) and 3-furaldehyde (8.65 mL) are added to potassium hydroxide (11.2 g) and H2O (0.45 mL) in acetonitrile (150 mL). The reaction mixture is heated to 60° C. for 2.5 h. The reaction mixture is allowed to cool to room temperature. The precipitate is filtered off, and the filtrate is concentrated in vacuo. The resulting crude epoxide (10.747 g) is dissolved in methanol (50 mL) and added to a 2.0 M solution of methylamine in methanol (100 mL). The reaction mixture is stirred at room temperature for 3 d and then heated to reflux for 30 min. The reaction mixture is allowed to cool to room temperature and is concentrated in vacuo. The resulting brown oil was purified via column chromatography (CHCl3/methanol, 95/5, 90/10; CHCl3/methanol/NH4OH, 90/10/1) to yield 2.703 g (19%) of the title compound as a yellow oil.

1. temperatureto cool to room temperature
2. filtrationThe precipitate is filtered off
3. concentrationthe filtrate is concentrated in vacuo
4. dissolutionThe resulting crude epoxide (10.747 g) is dissolved in methanol (50 mL)
5. additionadded to a 2.0 M solution of methylamine in methanol (100 mL)
6. temperatureheated
7. temperatureto reflux for 30 min
8. temperatureto cool to room temperature
9. concentrationis concentrated in vacuo
10. customThe resulting brown oil was purified via column chromatography (CHCl3/methanol, 95/5, 90/10; CHCl3/methanol/NH4OH, 90/10/1)

ORD record

ord-3f3c04bad60e414b8dc66d5d8769618c

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852731B2