Diisobutylaluminum hydride → HCID 14948472, compound

Temperature

-10 °C

To a solution of N,N-dimethyl-3-bromo-2-(bromomethyl) proprionic amide (44 g) in CH2Cl2 (300 mL) was added DIBAL (450 mL, 1.0 M in toluene) at −40° C. over 30 minutes. The mixture was allowed to warm to −10° C. over 3 hours and the diluted with CH2Cl2 (1500 mL). The reaction was quenched with a mixture of water (300 mL) and methanol (100 mL) at −10° C., followed by stirring at a temperature less that 10° C. for 2 hours. The suspension was filtered, dried, and concentrated to ca. 300 mL. The product crystallized upon standing overnight at room temperature. The crystals were separated from the solution and dried (19 g, 66%). MS(M+1): 178.

1. customThe reaction was quenched with a mixture of water (300 mL) and methanol (100 mL) at −10° C.
2. filtrationThe suspension was filtered
3. customdried
4. concentrationconcentrated to ca. 300 mL
5. customThe product crystallized
6. waitupon standing overnight at room temperature
7. customThe crystals were separated from the solution
8. customdried (19 g, 66%)

ORD record

ord-1a61fb269e9f4ee5837988d13d32f1ae

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024028B2