Acetyl chloride → (R)-1-methoxy-4,4-dimethyl-1-oxopentan-3-aminium chloride

Temperature

65 °C

(R)-3-amino-4,4-dimethylpentanoic acid, 2a, was dissolved in methanol (1.4 L). The solution was cooled in an ice bath and acetyl chloride (67.0 mL, 947.0 mmol) was added dropwise (maintaining the temperature below 10° C.). The reaction mixture was heated to 65° C. and stirred at that temperature for 3 h. The reaction mixture was cooled to room temperature and then flushed with toluene to remove volatiles. The crude material was used without further purification: 1H NMR (400 MHz, MeOH-d4) δ 3.75 (s, 3H), 3.41 (t, 1H), 2.88 (dd, 1H), 2.64-2.46 (m, 1H), 1.04 (s, 9H).

1. temperatureThe solution was cooled in an ice bath
2. temperaturemaintaining the temperature below 10° C.)
3. temperatureThe reaction mixture was cooled to room temperature
4. customflushed with toluene
5. customto remove volatiles
6. customThe crude material was used without further purification

ORD record

ord-cbab1d4ac9b747cd82153e22cf98a480

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394302B2