Aluminium lithium hydride → HCID 18518295, compound

A suspension of 3-(2-aminopyridin-4-yl)propanoic acid hydrochloride (0.73 g. 3.60 mmol, prepared according to WO94/14776 in THF (10 mL) was added over 45 min to lithium aluminum hydride (12 mL, 12 mmol, 1M in THF) at 0° C. The ice bath was removed and the reaction was allowed to stir at RT for 4.5 h. The reaction was cooled to 0° C. diluted with toluene (22 mL) and quenched by the sequential addition of H2O (0.86 mL) and NaF (1.54 g). The resulting suspension was stirred at 0° C. for 45 min. The reaction mixture was filtered and the precipitate was washed with additional 10% MeOH in CHCl3. The combined filtrates were concentrated under reduced pressure. Flash chromatography (10% MeOH/CHCl3, silica gel) gave 0.25 g of the desired material as a clear oil: MS(ES+) m/z 152.7 [M+H]+.

1. custom3.60 mmol, prepared
2. customThe ice bath was removed
3. temperatureThe reaction was cooled to 0° C.
4. additiondiluted with toluene (22 mL)
5. customquenched by the sequential addition of H2O (0.86 mL) and NaF (1.54 g)
6. stirringThe resulting suspension was stirred at 0° C. for 45 min
7. filtrationThe reaction mixture was filtered
8. washthe precipitate was washed with additional 10% MeOH in CHCl3
9. concentrationThe combined filtrates were concentrated under reduced pressure

ORD record

ord-44442e54a4b6407c9e54aa5965144e0d

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576643B2