Dimethylamine → (S)-2-tert-Butoxycarbonylamino-4-dimethylaminobutyric acid methyl ester

Temperature

60 °C

To a solution of (S)-4-bromo-2-tert-butoxycarbonylamino-butyric acid methyl ester (27.5 g, 93 mmol) in THF (100 mL) in a pressure reaction vessel was added triethylamine (26 mL) and dimethylamine (93 mL of 2.0 M in THF). The reaction vessel was sealed and heated to 60° C. for 16 hours and then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and then dissolved in dichloromethane (500 mL). The solution was washed with water (3×200 mL) and brine (200 mL), dried over MgSO4, filtered through Celite and concentrated under reduced pressure. The residue was dried under high vacuum to afford 23.4 g of yellow oil (97% yield).

1. customThe reaction vessel was sealed
2. temperaturecooled to room temperature
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. dissolutiondissolved in dichloromethane (500 mL)
5. washThe solution was washed with water (3×200 mL) and brine (200 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered through Celite
8. concentrationconcentrated under reduced pressure
9. customThe residue was dried under high vacuum

ORD record

ord-349ba96b543d427eab3e13b534e2790b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518983B2