Dimethylformamide → HCID 89479126, compound

Temperature

-78 °C

5 g of the compound [1-1] was dissolved in 100 mL of tetrahydrofuran and cooled to −78° C. Thereafter, 31.2 mL of n-butyllithium (1.6 M hexane solution) was added thereto, and the mixture was stirred for 1 hour at the same temperature. 774 μL of N, N-dimethylformamide was added to the produced white suspension, which was stirred for 5 hours while gradually heating back to room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-50/50), to obtain 514 mg of tert-butyl[(1S)-1-(4-formylphenyl) ethyl]carbamate [15-1] (hereinafter, referred to as the compound [15-1]) as a pale yellow amorphous.

1. stirringwas stirred for 5 hours
2. temperaturewhile gradually heating back to room temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe obtained organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe insolubles were filtered
7. concentrationthe filtrate was concentrated under reduced pressure
8. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-50/50)

ORD record

ord-e52d11fe9a11486cb67a1b585d02f6a5

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2