Trifluoroacetic acid → 2-(trans-Dec4-en-1-ylamino)acetaldehyde dimethyl acetal

trans-4-Decenal (7.2 g, 46.6 mmol) was mixed with 40 mL (0.37 moL) of aminoacetaldehyde dimethylacetal in 400 mL of methanol and stirred at room temperature for 30 minutes. NaCNBH3 (2.9 g, 46.6 mmol) was added, the reaction was cooled in an ice bath, and 27 mL (0.35 moL) of TFA was added dropwise over 5 minutes. The ice bath was then removed and the reaction was stirred for 70 minutes at room temperature, concentrated to a third of its volume, and partitioned between ethyl acetate (250 mL),and 1N NaOH (200 mL). The organic layer was washed with water (3×75 mL), dried over MgSO4, filtered and concentrated under reduced pressure to yield 11.1 g (45.6 mmol) of 2-(trans-dec-4-en-1-ylamino)acetaldehyde dimethyl acetal as a yellow oil that was used directly in the next step.

1. temperaturethe reaction was cooled in an ice bath
2. customThe ice bath was then removed
3. stirringthe reaction was stirred for 70 minutes at room temperature
4. concentrationconcentrated to a third of its volume
5. custompartitioned between ethyl acetate (250 mL),and 1N NaOH (200 mL)
6. washThe organic layer was washed with water (3×75 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-6a29aae71d0142869b7156acf0b15c1e

Quelldatensatz

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06949681B2