2-Amino-2-methyl-1-propanol → HCID 15145670, compound

Temperature

2.5 °C

To a stirred solution of H2NC(CH3)2CH2OH (16.8 g, 188 mmol) in CHCl3 (150 mL),under nitrogen at 0° C., acryloyl chloride (8.5 g, 94 mmol) (filtered over basic alumna) was added drop-wise via an addition funnel in such a way that the temperature did not exceed 5° C. (˜1.5 h). After complete addition, the reaction mixture was stirred for ˜2 h at 0-5° C., brought to room temperature, filtered and the filtrate concentrated by rotary evaporation. The residue was treated with 75 ml CHCl3 and ˜20 g basic alumina. This mixture was stirred for 0.5 h at room temperature (20-25° C.) and filtered. The alumina was washed with 2×10 mL CHCl3 and the combined filtrate was concentrated at reduced pressure to afford CH2═CHC(O)NHC(CH3)2CH2OH (13.5 g ) as a semisolid material. This material was used in the next step without further purification. 1H NMR (CDCl3) spectral data is consistent with the structure; δ 6.27 (br s, overlaps, 1H), 6.24 (dd, 1H), 6.14 (dd, 1H), 5.63 (dd, 1H), 4.88 (brs, 1H), 3.59 (s, 2H), 1.3 1 (s, 6H) ppm.

1. customdid not exceed 5° C.
2. custom(˜1.5 h)
3. additionAfter complete addition
4. custombrought to room temperature
5. filtrationfiltered
6. concentrationthe filtrate concentrated by rotary evaporation
7. additionThe residue was treated with 75 ml CHCl3 and ˜20 g basic alumina
8. stirringThis mixture was stirred for 0.5 h at room temperature (20-25° C.)
9. filtrationfiltered
10. washThe alumina was washed with 2×10 mL CHCl3
11. concentrationthe combined filtrate was concentrated at reduced pressure

ORD record

ord-377e0090890c42e3935c5ee18bd1bb33

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800788B2