Dimethylformamide → HCID 58739156, compound

Temperature

-78 °C

To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (2 g, 6.66 mmol) in THF (20 mL) at −78° C. was added methyllithium (4.72 mL, 1.4M in Et2O, 6.66 mmol), and the reaction mixture was stirred at −78° C. for 5 min. tert-Butyllithium (7.76 mL, 1.7 M in pentane, 13.32 mmol) was added, and the reaction mixture was stirred at −78° C. for 15 min. Dimethylformamide (1.7 mL, 13.32 mmol) was added rapidly, and the reaction mixture was warmed slowly to room temperature over a period of 1 h. NH4Cl (sat.) (100 mL) was added, the resulting mixture was extracted with ethyl acetate (3×100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the filtrated was evaporated in vacuo to give the title compound (1.6 g, 96% yield) as yellow crystals.

1. additionwas added
2. temperaturethe reaction mixture was warmed slowly to room temperature over a period of 1 h
3. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customthe filtrated was evaporated in vacuo

ORD record

ord-b018b0075b674d449bca5dd69c540ce7

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135472B2