Aluminium lithium hydride → HCID 58446425, compound

Temperature

0 °C

N-(2,5-anhydro-D-allonoyl)-4-methoxy-N-methyl-aniline (0.7 g, 2.4 mmol) was dissolved in anhydrous THF (80 mL) and the solution was cooled to 0° C. After 10 minutes, a lithium aluminium hydride solution (9.6 mL, 1M) in THF was added slowly over a period of 5 to 7 minutes and the resulting mixture was stirred for 1 hour. The reaction temperature was raised slowly from 0° C. to room temperature and stirring was continued for an additional 2 hours. The progress of the reaction was monitored by HPLC and the reaction was quenched carefully with water (300 mL) and adjusted to pH 7.5 with 1M HCl. The solids were separated by centrifugation and the residue was washed with water (2×50 mL). The combined solutions were evaporated in vacuo and the residue was treated with methanol (100 mL). The remaining solid was again separated by filtration and the filtrate was evaporated to dryness. The residue was purified by RP HPLC and evaporation of the appropriate fractions yielded the title compound as a yellow oil (170 mg, 0.6 mmol, 25%): MS (ES) m/z 284 [M+H]+, 306 [M+Na]+.

1. temperatureThe reaction temperature was raised slowly from 0° C. to room temperature
2. stirringstirring
3. waitwas continued for an additional 2 hours
4. customthe reaction was quenched carefully with water (300 mL)
5. customThe solids were separated by centrifugation
6. washthe residue was washed with water (2×50 mL)
7. customThe combined solutions were evaporated in vacuo
8. additionthe residue was treated with methanol (100 mL)
9. customThe remaining solid was again separated by filtration
10. customthe filtrate was evaporated to dryness
11. customThe residue was purified by RP HPLC and evaporation of the appropriate fractions

ORD record

ord-caf1851384184dfb84013cd8eaccb52f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255121B2