Methanol → HCID 178419191, compound

Trimethylamine-methylcyanoborane (0.71 g, 4.20 mmol) in anhydrous dichloromethane (2.0 ml) was taken with a solution of triethyloxonium tetrafluoroborate (3.8 ml of 2.22 M solution in dichloromethane), under a static atmosphere of nitrogen. The mixture was stirred at room temperature for 24 h. It was cooled to 0° C., slowly brought to pH=11 by addition of 1 N NaOH and stirred at 0° C. After ca 0.25 h, it was diluted with dichloromethane (ca 15 ml) and 1 N NaOH (ca 20 ml) and stirred at room temperature for 2 days. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×35 ml). The organic extracts were combined, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to give an oil. The product was purified by dry flash chromatography on silica gel using dichloromethane (4×25 ml), followed by dichloro-methane:acetone (8:2, 4×25 ml) and finally dichloromethane:methanol (8:2, 10×35 ml). The product was obtained as a clear colorless oil from dichloro-methane:methanol fractions. Yield 0.58 g, 87.37%. The product could also be purified by normal flash chromatography on silica gell using diethylether:dichloromethane (9:1, 500 ml) followed by dichloromethane-methanol (8:2, 500 ml) with similar yield.

1. temperatureIt was cooled to 0° C.
2. stirringstirred at 0° C
3. waitAfter ca 0.25 h
4. stirringstirred at room temperature for 2 days
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (2×35 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure
9. customto give an oil
10. customThe product was purified
11. customby dry flash chromatography on silica gel
12. customThe product was obtained as a clear colorless oil from dichloro-methane
13. customThe product could also be purified by normal flash chromatography on silica gell using diethylether:dichloromethane (9:1, 500 ml)

ORD record

ord-463ee8aeb01b4c35bf2030b4cdc42870

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05023513