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

trans4-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 record

ord-1ce89573e568443dab511de42908e990

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06444786B1