Aluminium lithium hydride → (S)-2-(dibenzylamino)butanal

Temperature

-30 °C

Under an atmosphere of argon, at −20 to −30° C., LiAlH4 (2.34 g, 61.8 mmol, Eq: 1.2) was combined with THF (150 ml) to give a light grey suspension. Then (S)-2-(dibenzylamino)-N-methoxy-N-methylbutanamide (24 g, 51.5 mmol, Eq: 1.00), diluted in THF (50 ml) was added at −30° C. The reaction was stirred for 2.5 h at −30° C. The excess reagent was quenched by the dropwise addition of ethyl acetate and water (1/1, ˜30 ml). The reaction was vigorously stirred for 15 min at RT. After filtration through dicalite, the mixture was diluted with water (100 ml) and extracted with ethyl acetate. The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a light brown liquid (13.41 g, 97.5%, MS (m/e)=268.3 [M+H+]).

1. customat −20 to −30° C.
2. customto give a light grey suspension
3. additionwas added at −30° C
4. customThe excess reagent was quenched by the dropwise addition of ethyl acetate and water (1/1, ˜30 ml)
5. stirringThe reaction was vigorously stirred for 15 min at RT
6. filtrationAfter filtration through dicalite
7. additionthe mixture was diluted with water (100 ml)
8. extractionextracted with ethyl acetate
9. dry with materialThe organic layers were dried over Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-210e70855d4d4770add883072f1a7b5b

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729061B2